(2R,4S)-1-p-Nitrobenzyloxycarbonyl-2-(4-t-butyloxycarbonylbutyl)-4-acetylthiopyrrolidine → (2R,4S)-1-p-nitrobenzyloxycarbonyl-2-(4-carboxybutyl)-4-acetylthiopyrrolidine

HRID 1088283Notes

Reaction equation

HRID 1088283 reaction equation
[N+:1]([C:4]1[CH:33]=[CH:32][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]>FC(F)(F)C(O)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:11])=[CH:32][CH:33]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 15671523(2R,4S)-1-p-Nitrobenzyloxycarbonyl-2-(4-t-butyloxycarbonylbutyl)-4-acetylthiopyrrolidine

Product 1

HCID 15671524(2R,4S)-1-p-nitrobenzyloxycarbonyl-2-(4-carboxybutyl)-4-acetylthiopyrrolidine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(2R,4S)-1-p-Nitrobenzyloxycarbonyl-2-(4-t-butyloxycarbonylbutyl)-4-acetylthiopyrrolidine (493 mg) was dissolved in 2.5 ml of trifluoroacetic acid, followed by stirring at room temperature for 15 minutes. The reaction mixture was distilled off to obtain (2R,4S)-1-p-nitrobenzyloxycarbonyl-2-(4-carboxybutyl)-4-acetylthiopyrrolidine.

Workup

  1. distillationThe reaction mixture was distilled off

Sources & evidence

ORD record
ord-b76b80c2e41a4ce9bb00875e3ccf3f5c
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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