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

HRID 256033Notes

Reaction equation

[CH2:1]([O:8][C:9]([CH:11]([NH:20][C@H:21]1[CH2:27][S:26][CH2:25][C@@H:24]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)[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]([C@@H:11]([NH:20][C@H:21]1[CH2:27][S:26][CH2:25][C@@H:24]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)[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

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 70354705t-Butyl alpha-[6(R)-(1-benzyloxycarbonyl-3-phenylpropylamino)-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate

Product 1

HCID 70364915alpha-{6(R)-[1(S)-Benzyloxycarbonyl-3-phenylpropylamino]-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetic acid

Procedure

158 mg of isomer B of t-butyl α-[6(R)-(1-benzyloxycarbonyl-3-phenylpropylamino)-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate (prepared as described in Example 25) were treated with trifluoroacetic acid to remove its t-butyl group in the same manner as described in Example 3. The title compound was obtained as an amorphous solid in a yield of 109 mg.

Workup

customto remove its t-butyl group in the same manner

Sources & evidence

ORD record: ord-1d94cea0efdf420397d7c599de1f5dc2
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

Loading…