Ethyl Acetate → t-Butyl alpha-{6-[1-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl}acetate

HRID 256013Notes

Reaction equation

HRID 256013 reaction equation
[NH2:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][N:4]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:3]1=[O:23].Br[CH:25]([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(OCC)(=O)C>C(Cl)Cl>[CH2:29]([O:28][C:26]([CH:25]([NH:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][N:4]([CH2:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[C:3]1=[O:23])[CH2:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11747666Benzenebutanoic acid, alpha-bromo-, ethyl esterHCID 14423825t-Butyl alpha-(6-amino-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl)acetate

Product 1

HCID 13877894t-Butyl alpha-{6-[1-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl}acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.22 g of the isomer of t-butyl α-[6-amino-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl]acetate [prepared as described in step (h) above] was subjected to N-alkylation with 0.28 g of ethyl 2-bromo-4-phenylbutyrate in the same manner as described in Example 1(h). The resulting product was subjected to silica gel column chromatography, using a 1:20 by volume mixture of ethyl acetate and methylene chloride as the eluent. From the fraction first eluted was obtained 0.14 g of t-butyl α-{6-[1-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl}acetate as an oil.

Workup

  1. washFrom the fraction first eluted

Sources & evidence

ORD record
ord-2ca9a8bffb97460ba122fa637c890d67
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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