Hydrochloric Acid → (2S, 4S)-2-(3-aminoazetidin-1-ylcarbonyl)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride

HRID 362109Notes

Reaction equation

HRID 362109 reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([C:6]([C@@H:8]2[CH2:12][C@H:11]([S:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:10][N:9]2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])=[O:7])[CH2:3]1.[ClH:36].C(OCC)C>C(OCC)(=O)C>[ClH:36].[NH2:1][CH:2]1[CH2:5][N:4]([C:6]([C@@H:8]2[CH2:12][C@H:11]([S:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH2:10][N:9]2[C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=2)=[O:24])=[O:7])[CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 11145523(2S,4S)-2-(3-Aminoazetidin-1-ylcarbonyl)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 67630253(2S, 4S)-2-(3-aminoazetidin-1-ylcarbonyl)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

0.78 g of (2S, 4S)-2-(3-aminoazetidin-1-ylcarbonyl)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in Preparation 113(a)] was dissolved in 15 ml of ethyl acetate, and 0.78 ml of a 4N solution of hydrogen chloride in ethyl acetate was added to the resulting solution, whilst ice-cooling. Diethyl ether was added to the reaction mixture, and the resulting powder was filtered off and dried, to give 0.79 g of (2S, 4S)-2-(3-aminoazetidin-1-ylcarbonyl)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride.

Workup

  1. temperaturecooling
  2. filtrationthe resulting powder was filtered off
  3. customdried

Sources & evidence

ORD record
ord-5cb8702decdf4ee4887c11ef1cebfa8d
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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