Trifluoroacetic acid → alpha-{6(R)-[1(S)-Ethoxycarbonyl-3-phenylpropylamino]-3(R)-isopropyl-5-oxoperhydro-1,4-thiazepin-4-yl}acetic acid

HRID 256035Notes

Reaction equation

[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]1[CH2:22][S:21][CH2:20][C@@H:19]([CH:23]([CH3:25])[CH3:24])[N:18]([CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])[C:17]1=[O:34])[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]([CH:23]([CH3:24])[CH3:25])[N:18]([CH2:26][C:27]([OH:29])=[O:28])[C:17]1=[O:34])[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 18610542t-butyl alpha-{6(R)-[1(S)-ethoxycarbonyl-3-phenylpropylamino]-3(R)-isopropyl-5-oxoperhydro-1,4-thiazepin-4-yl}acetate

Product 1

HCID 18610525alpha-{6(R)-[1(S)-Ethoxycarbonyl-3-phenylpropylamino]-3(R)-isopropyl-5-oxoperhydro-1,4-thiazepin-4-yl}acetic acidYield 91.7%

Procedure

0.32 g of t-butyl α-{6(R)-[1(S)-ethoxycarbonyl-3-phenylpropylamino]-3(R)-isopropyl-5-oxoperhydro-1,4-thiazepin-4-yl}acetate (isomer B) synthesized as described in Example 27 was subjected to de-t-butylation with trifluoroacetic acid in the same manner as described in Example 3, to give 260 mg of the title compound as an amorphous solid.

Sources & evidence

ORD record: ord-5819d037a29f45de8c4e39a008eda144
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

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