Hydrochloric Acid → (2S,4S)-4-(4-Methoxybenzylthio)-2-[(3S)-3-aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine Hydrochloride

HRID 362038Notes

Reaction equation

HRID 362038 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:37]=[CH:36][C:7]([CH2:8][S:9][C@@H:10]2[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=3)=[O:16])[C@H:12]([C:28]([N:30]3[CH2:34][CH2:33][C@H:32]([NH2:35])[CH2:31]3)=[O:29])[CH2:11]2)=[CH:6][CH:5]=1>C(OCC)(=O)C>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][S:9][C@@H:10]2[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=3)=[O:16])[C@H:12]([C:28]([N:30]3[CH2:34][CH2:33][C@H:32]([NH2:35])[CH2:31]3)=[O:29])[CH2:11]2)=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67586148(2S,4S)-4-(4-Methoxybenzylthio)-2-[(3S)-3-aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 67586147(2S,4S)-4-(4-Methoxybenzylthio)-2-[(3S)-3-aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine Hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

4.37 ml of a 4N solution of hydrogen chloride in ethyl acetate were added, whilst ice-cooling, to a solution of 3.00 g of (2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-3-aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (i) above] in 30 ml of ethyl acetate, and the resulting mixture was stirred at the same temperature for 30 minutes. At the end of this time, it was diluted with ethyl acetate, and the powder which precipitated was collected by filtration and dried, to give 3.20 g of the title compound, as a powder.

Workup

  1. customthe powder which precipitated
  2. filtrationwas collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-e840ef5831b943d88df0f2e3173735b5
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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