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

HRID 256029Notes

Reaction equation

HRID 256029 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:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24][N:23]([CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])[C:22]1=[O:42])[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:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24][N:23]([CH2:34][C:35]([OH:37])=[O:36])[C:22]1=[O:42])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20164783t-Butyl alpha-[6-(1-benzyloxycarbonyl-3-phenylpropylamino)-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl]acetate

Product 1

HCID 20164782alpha-[6-(1-Benzyloxycarbonyl-3-phenylpropylamino)-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl]acetic acid

Procedure

0.10 g of isomer B of t-butyl α-[6-(1-benzyloxycarbonyl-3-phenylpropylamino)-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl]acetate (prepared as described in Example 21) was treated with trifluoroacetic acid to remove its t-butyl group by the process described in Example 3. 70 mg of the title compound were obtained as amorphous solid.

Workup

  1. customto remove its t-butyl group by the process

Sources & evidence

ORD record
ord-8c19cee1d5334ba3b06ae69c219ab119
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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