Thioglycolic Acid → (2R,4R)-4-Acetylthio-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 362081Notes

Reaction equation

HRID 362081 reaction equation
N(C(OCC)=O)=NC([O:5][CH2:6][CH3:7])=O.O[C@@H:14]1[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[C@@H:16]([C:32]([N:34]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][O:42][C:43]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=3)=[O:44])[CH2:36][CH2:35]2)=[O:33])[CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[SH:75]CC(O)=O>O1CCCC1>[C:6]([S:75][C@H:14]1[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[C@@H:16]([C:32]([N:34]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][O:42][C:43]([O:45][CH2:46][C:47]3[CH:48]=[CH:49][C:50]([N+:53]([O-:55])=[O:54])=[CH:51][CH:52]=3)=[O:44])[CH2:36][CH2:35]2)=[O:33])[CH2:15]1)(=[O:5])[CH3:7]

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86753701(2R,4S)-4-Hydroxy-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 86753702(2R,4R)-4-Acetylthio-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 421 mg of diethyl azodicarboxylate in 1.2 ml of tetrahydrofuran was added dropwise, whilst ice-cooling, to a solution of 1.21 g of (2R,4S)-4-hydroxy-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine and 634 mg of triphenylphosphine in 8 ml of tetrahydrofuran, and the resulting mixture was stirred at the same temperature for 10 minutes. 171 μl of mercaptoacetic acid were then added dropwise to the mixture, and the mixture was stirred at room temperature for 1 hour. Following the same procedure as described in Preparation 57(ii), the reaction mixture was worked up and purified, to give 1.04 g of the title compound, as a colorless powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. custompurified

Sources & evidence

ORD record
ord-6a3c3be6f2434c87a3bcde3eca154a40
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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