HCID 13854085, compound → t-Butyl alpha-[6-(1-benzyloxycarbonyl-3-phenylpropylamino)-2-(2-furyl)-5-oxoperhydro-1,4-thiazepin-4-yl]acetate

HRID 256077Notes

Reaction equation

HRID 256077 reaction equation
[NH2:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[O: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]>C(OCC)(=O)C.C(Cl)Cl>[CH2:28]([O:27][C:25]([CH:24]([NH:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[O: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

5

Reactant 2

HCID 13854085HCID 13854085, compoundHCID 19024556Benzyl 2-bromo-4-phenylbutyrate

Product 1

HCID 20164970t-Butyl alpha-[6-(1-benzyloxycarbonyl-3-phenylpropylamino)-2-(2-furyl)-5-oxoperhydro-1,4-thiazepin-4-yl]acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure described in Example 42(h), 0.30 g of t-butyl α-[6-amino-2-(2-furyl)-5-oxoperhydro-1,4-thiazepin-4-yl]acetate [obtained as described in Example 56(f)] was N-alkylated using 0.60 g of benzyl 2-bromo-4-phenylbutyrate. The resulting product was subjected to silica gel column chromatography, using a 1:40 by volume mixture of ethyl acetate and methylene chloride as eluent, to separate it into two isomers, A and B, (ascribed to the asymmetric carbon atom to which the phenethyl group is attached).

Workup

  1. customto separate it into two isomers

Sources & evidence

ORD record
ord-55e3d8846b8f4879b891719ab34d3d66
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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