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

HRID 256031Notes

Reaction equation

[CH2:1]([O:5][C:6]([CH:8]([NH:17][C@H:18]1[CH2:24][S:23][CH2:22][C@@H:21]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)[N:20]([CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[C:19]1=[O:38])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>>[CH2:1]([O:5][C:6]([C@@H:8]([NH:17][C@H:18]1[CH2:24][S:23][CH2:22][C@@H:21]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)[N:20]([CH2:30][C:31]([OH:33])=[O:32])[C:19]1=[O:38])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 54230584t-Butyl alpha-[6(R)-(1-butoxycarbonyl-3-phenylpropylamino)-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate

Product 1

HCID 53822035alpha-{6(R)-[1(S)-Butoxycarbonyl-3-phenylpropylamino]-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetic acid

Procedure

100 mg of isomer B of t-butyl α-[6(R)-(1-butoxycarbonyl-3-phenylpropylamino)-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate (prepared as described in Example 23) was treated with trifluoroacetic acid to remove its t-butyl group in the same manner as in Example 3. 60 mg of the title compound were obtained as an amorphous solid.

Workup

customto remove its t-butyl group in the same manner as in Example 3

Sources & evidence

ORD record: ord-f4b86ae400584aa29546eacdf6107aad
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

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