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

HRID 256024Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]([NH:15][C@H:16]1[CH2:22][S:21][CH2:20][C@@H:19]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[N:18]([CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[C:17]1=[O:36])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>>[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]1[CH2:22][S:21][CH2:20][C@@H:19]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[N:18]([CH2:28][C:29]([OH:31])=[O:30])[C:17]1=[O:36])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 53995810t-Butyl alpha-{6(R)-[1-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetate

Product 1

HCID 13877956alpha-{6(R)-[1(S)-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl)acetic acid

Procedure

160 mg of isomer B of t-butyl α-{6(R)-[1-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetate [prepared as described in Example 16(h)] were subjected to de-t-butylation with trifluoroacetic acid in the manner described in Example 3, to give 118 mg of the title compound as an amorphous solid.

Sources & evidence

ORD record: ord-56eb5e58c44149d1b4acabc823e3021c
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

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