Trifluoroacetic acid → alpha-[6-(1-Benzyloxycarbonyl-3-phenylpropylamino)-5-oxo-2-(3-thienyl)perhydro-1,4-thiazepin-4-yl]acetic acid

HRID 256059Notes

Reaction equation

HRID 256059 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([NH:20][CH:21]1[CH2:27][S:26][CH:25]([C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)[CH2:24][N:23]([CH2:33][C:34]([O:36]C(C)(C)C)=[O:35])[C:22]1=[O:41])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[CH2:1]([O:8][C:9]([CH:11]([NH:20][CH:21]1[CH2:27][S:26][CH:25]([C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)[CH2:24][N:23]([CH2:33][C:34]([OH:36])=[O:35])[C:22]1=[O:41])[CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20164794t-Butyl alpha-[6-(1-benzyloxycarbonyl-3-phenylpropylamino)-5-oxo-2-(3-thienyl)perhydro-1,4-thiazepin-4-yl]acetate

Product 1

HCID 20164901alpha-[6-(1-Benzyloxycarbonyl-3-phenylpropylamino)-5-oxo-2-(3-thienyl)perhydro-1,4-thiazepin-4-yl]acetic acid

Procedure

180 mg of isomer B of t-butyl α-[6-(1-benzyloxycarbonyl-3-phenylpropylamino)-5-oxo-2-(3-thienyl)perhydro-1,4-thiazepin-4-yl]acetate were treated with trifluoroacetic acid by the procedure described in Example 43, to remove the t-butyl group and give 140 mg of the title compound as a powder.

Workup

  1. customto remove the t-butyl group

Sources & evidence

ORD record
ord-7e19d74d7e91428bb2906702cb4d89ca
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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