Benzene → t-butyl alpha-{6(R)-[8-t-butoxycarbonylamino-1(R)-ethoxycarbonyloctylamino]-5-oxo-2(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetate

HRID 868243Notes

Reaction equation

HRID 868243 reaction equation
[NH2:1][C@H:2]1[CH2:8][S:7][C@H: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]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:25]([O:27][CH2:28][CH3:29])=[O:26].C1C=CC=CC=1>C(OCC)(=O)C>[C:41]([O:40][C:38]([NH:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][C@@H:24]([NH:1][C@H:2]1[CH2:8][S:7][C@H: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])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:39])([CH3:44])([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 241BenzeneHCID 13854082tert-Butyl (2S,6R)-6-amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepine-4-acetateHCID 21287862HCID 21287862, compound

Product 1

HCID 70410007t-butyl alpha-{6(R)-[8-t-butoxycarbonylamino-1(R)-ethoxycarbonyloctylamino]-5-oxo-2(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetateYield 9.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.3 g of t-butyl α-[6(R)-amino-5-oxo-2(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate was treated with 1.73 g of ethyl 2-bromo-9-t-butoxycarbonylaminononanoate prepared as described in Preparation 4) in a similar manner to that described in Example 4. The product was then subjected to column chromatography through silica gel using a mixture of benzene and ethyl acetate in the ratio 5:1 by volume as the eluent. 237 mg of t-butyl α-{6(R)-[8-t-butoxycarbonylamino-1(R)-ethoxycarbonyloctylamino]-5-oxo-2(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetate was obtained as a syrup from the fractions eluted first.

Workup

  1. customprepared
  2. customas described in Preparation 4) in a similar manner to that

Sources & evidence

ORD record
ord-baf9630151de420b8ac55e5a65d2a5d5
Source dataset
uspto-grants-1988_10
Patent number
US04778790

Reaction notes

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