Abstract
Highly preservable amino protecting reagents derived from the 2-oxazolone moiety as a common activating mediator have been developed. 3-Alkoxycarbonyl-2-oxazolones serve as easily handled reagents for amino protection, including tert-butoxycarbonylation, benzyloxycarbonylation, p-methoxybenzyloxycarbonylation, methoxycarbonylation and ethoxycarbonylation. For example, high yield N-protection of α-amino acids has been smoothly performed by the use of 3-tert-butoxycarbonyl [Boc-Ox] and 3-benzyloxycarbonyl-2-oxazolones Cbz-Ox] in aqueous solution at room temperature. A series of homopolymers, poly(3-alkoxycarbonyl-2-oxazolone), is readily obtainable by radical-initiated chain reaction of the corresponding 4,5-unsubstituted oxazolone monomers (except for the tert-butoxy derivative, which failed to give polymeric compounds), and these were successfully used for amino protection as well. Use of the polymer reagents greatly simplifies the purification procedure, though a longer reaction time is required.
| Original language | English |
|---|---|
| Pages (from-to) | 2174-2181 |
| Number of pages | 8 |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 32 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 1984 |
| Externally published | Yes |
Fingerprint
Keywords
- 3-alkoxycarbonyl-2-oxazolone
- 3-benzyloxycarbonyl-2-oxazolone
- 3-tertbutoxycarbonyl-2-oxazolone
- amino protection
- poly(2-alkoxycarbonyl-2-oxazolone)
ASJC Scopus subject areas
- Chemistry(all)
- Drug Discovery
Cite this
3-Alkoxycarbonyl-2-oxazolones and Their Homopolymers as Highly Preservable Amino-Protecting Reagents. tert-Butoxy-carbonylation and Benzyloxycarbonylation of Amino Groups. / Kunieda, Takehisa; Higuchi, Tsunehiko; Abe, Yoshihiro; Hirobe, Masaaki.
In: Chemical and Pharmaceutical Bulletin, Vol. 32, No. 6, 1984, p. 2174-2181.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - 3-Alkoxycarbonyl-2-oxazolones and Their Homopolymers as Highly Preservable Amino-Protecting Reagents. tert-Butoxy-carbonylation and Benzyloxycarbonylation of Amino Groups
AU - Kunieda, Takehisa
AU - Higuchi, Tsunehiko
AU - Abe, Yoshihiro
AU - Hirobe, Masaaki
PY - 1984
Y1 - 1984
N2 - Highly preservable amino protecting reagents derived from the 2-oxazolone moiety as a common activating mediator have been developed. 3-Alkoxycarbonyl-2-oxazolones serve as easily handled reagents for amino protection, including tert-butoxycarbonylation, benzyloxycarbonylation, p-methoxybenzyloxycarbonylation, methoxycarbonylation and ethoxycarbonylation. For example, high yield N-protection of α-amino acids has been smoothly performed by the use of 3-tert-butoxycarbonyl [Boc-Ox] and 3-benzyloxycarbonyl-2-oxazolones Cbz-Ox] in aqueous solution at room temperature. A series of homopolymers, poly(3-alkoxycarbonyl-2-oxazolone), is readily obtainable by radical-initiated chain reaction of the corresponding 4,5-unsubstituted oxazolone monomers (except for the tert-butoxy derivative, which failed to give polymeric compounds), and these were successfully used for amino protection as well. Use of the polymer reagents greatly simplifies the purification procedure, though a longer reaction time is required.
AB - Highly preservable amino protecting reagents derived from the 2-oxazolone moiety as a common activating mediator have been developed. 3-Alkoxycarbonyl-2-oxazolones serve as easily handled reagents for amino protection, including tert-butoxycarbonylation, benzyloxycarbonylation, p-methoxybenzyloxycarbonylation, methoxycarbonylation and ethoxycarbonylation. For example, high yield N-protection of α-amino acids has been smoothly performed by the use of 3-tert-butoxycarbonyl [Boc-Ox] and 3-benzyloxycarbonyl-2-oxazolones Cbz-Ox] in aqueous solution at room temperature. A series of homopolymers, poly(3-alkoxycarbonyl-2-oxazolone), is readily obtainable by radical-initiated chain reaction of the corresponding 4,5-unsubstituted oxazolone monomers (except for the tert-butoxy derivative, which failed to give polymeric compounds), and these were successfully used for amino protection as well. Use of the polymer reagents greatly simplifies the purification procedure, though a longer reaction time is required.
KW - 3-alkoxycarbonyl-2-oxazolone
KW - 3-benzyloxycarbonyl-2-oxazolone
KW - 3-tertbutoxycarbonyl-2-oxazolone
KW - amino protection
KW - poly(2-alkoxycarbonyl-2-oxazolone)
UR - http://www.scopus.com/inward/record.url?scp=0001730681&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0001730681&partnerID=8YFLogxK
U2 - 10.1248/cpb.32.2174
DO - 10.1248/cpb.32.2174
M3 - Article
AN - SCOPUS:0001730681
VL - 32
SP - 2174
EP - 2181
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
SN - 0009-2363
IS - 6
ER -