HCID 13854081, compound → HCID 20164804, compound

HRID 256067Notes

Reaction equation

[NH2:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][N:4]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:3]1=[O:22].Br[CH:24]([CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>>[CH2:28]([O:27][C:25]([CH:24]([NH:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][N:4]([CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C:3]1=[O:22])[CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Reactant 2

HCID 13854081HCID 13854081, compound

HCID 19024556Benzyl 2-bromo-4-phenylbutyrate

Product 1

HCID 20164804HCID 20164804, compound

Procedure

Following the same procedure described in Example 42(h), 0.4 g of t-butyl α-[6-amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate [prepared as described in Example 49(g)] was N-alkylated using 0.80 g of benzyl 2-bromo-4-phenylbutyrate. The resulting product was subjected to silica gel column chromatography eluted with a 1:40 by volume mixture of ethyl acetate and methylene chloride to separate it into two isomers, A and B, (ascribed to the asymmetric carbon atom to which the phenethyl group is attached).

Workup

washeluted with a 1:40 by volume mixture of ethyl acetate and methylene chloride
customto separate it into two isomers

Sources & evidence

ORD record: ord-d89d3909a60349ef86f1b84d062d1544
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

Loading…