Ethyl Acetate → t-Butyl alpha-[6-(1-ethoxycarbonyl-3-phenylpropylamino)-2-(2-naphthyl)-5-oxoperhydro-1,4-thiazepin-4-yl]acetate

HRID 256050Notes

Reaction equation

HRID 256050 reaction equation
[NH2:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)[CH2:5][N:4]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:3]1=[O:27].Br[CH:29]([CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31].C(OCC)(=O)C>C(Cl)Cl>[CH2:33]([O:32][C:30]([CH:29]([NH:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)[CH2:5][N:4]([CH2:19][C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[C:3]1=[O:27])[CH2:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:31])[CH3:34]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11747666Benzenebutanoic acid, alpha-bromo-, ethyl esterHCID 20164805t-Butyl alpha-[6-amino-2-(2-naphthyl)-5-oxoperhydro-1,4-thiazepin-4-yl]acetate

Product 1

HCID 20164859t-Butyl alpha-[6-(1-ethoxycarbonyl-3-phenylpropylamino)-2-(2-naphthyl)-5-oxoperhydro-1,4-thiazepin-4-yl]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.85 g of t-butyl α-[6-amino-2-(2-naphthyl)-5-oxoperhydro-1,4-thiazepin-4-yl]acetate [prepared as described in step (g) above] was subjected to N-alkylation with 1.08 g of ethyl 2-bromo-4-phenylbutyrate in the same manner as described in Example 36(h). The reaction product was subjected to silica gel column chromatography, using a 1:30 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

  1. customto separate it into two isomers

Sources & evidence

ORD record
ord-2b5b7d5a59114681b9a872afe74a267b
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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