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

HRID 256057Notes

Reaction equation

HRID 256057 reaction equation
[CH2:1]([O:5][C:6]([CH:8]([NH:17][CH:18]1[CH2:24][S:23][CH:22]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[CH2:21][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]([CH:8]([NH:17][CH:18]1[CH2:24][S:23][CH:22]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[CH2:21][N:20]([CH2:30][C:31]([OH:33])=[O:32])[C:19]1=[O:38])[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20164835t-Butyl alpha-[6-(1-butoxycarbonyl-3-phenylpropylamino)-5-oxo-2-(3-thienyl)perhydro-1,4-thiazepin-4-yl]acetate

Product 1

HCID 13854103alpha-[6-(1-Butoxycarbonyl-3-phenylpropylamino)-5-oxo-2-(3-thienyl)perhydro-1,4-thiazepin-4-yl]acetic acid

Procedure

130 mg of isomer B of t-butyl α-[6-(1-butoxycarbonyl-3-phenylpropylamino)-5-oxo-2-(3-thienyl)perhydro-1,4-thiazepin-4-yl]acetate (prepared as described in Example 45 above) were treated with trifluoroacetic acid by the same procedure as is described in Example 43 to remove the t-butyl group and give the title compound as a crystalline powder, melting at 156° C., in a yield of 70 mg.

Workup

  1. customto remove the t-butyl group

Sources & evidence

ORD record
ord-4f057cb1ba614c0abbfa50a827c7b416
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

Loading…