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

HRID 256026Notes

Reaction equation

HRID 256026 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]([CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:26]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[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])[CH2:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:27])[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14423825t-Butyl alpha-(6-amino-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl)acetateHCID 20164900HCID 20164900, compound

Product 1

HCID 20164825t-Butyl alpha-{6-[1-butoxycarbonyl-3-phenylpropylamino]-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl}acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.34 g of t-butyl α-(6-amino-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl)acetate [prepared as described in Example 7(g) above] was N-alkylated with 0.45 g of butyl 2-bromo-4-phenylbutyrate in the manner described in Example 1(h). The resulting product was subjected to silica gel column chromatography using a 1:40 by volume mixture of ethyl acetate and methylene chloride as the eluent. As a result, the title compound was separated into isomers A and B (resulting from the asymmetric carbon atom to which the phenethyl group is attached).

Workup

  1. customAs a result, the title compound was separated into isomers A and B (
  2. customresulting from the asymmetric carbon atom to which the phenethyl group

Sources & evidence

ORD record
ord-c2ddc43774cf4d98bb2918deb89cf98d
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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