Ethylene Oxide → Acetamide

HRID 615268Notes

Reaction equation

[O:1]1[CH2:3][CH2:2]1.[C:4]([NH:7][C@H](C(O)=O)C[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:6])[CH3:5]>>[CH2:3]1[O:1][CH:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:4]([NH2:7])(=[O:6])[CH3:5]

Participants

Reactant 2

HCID 6354Ethylene Oxide

HCID 74839N-Acetyl-L-phenylalanine

Product 2

HCID 178Acetamide

HCID 7276Styrene Oxide

Procedure

According to the process of this invention described hereinabove, the N-acyl-α-amino acid of formula (I) can be produced in good yields in one step from the oxirane (II) and the amide compound (III) with great industrial advantage. For example, according to the process of this invention, N-acetylphenylalanine can be obtained in a yield of as high as 72 to 98% from styrene oxide and acetamide as will be seen from Examples given hereinafter.

Sources & evidence

ORD record: ord-ac0c04f911d74be48228716e5e5510c5
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04497964

Reaction notes

Loading…