Hydrochloric Acid → HCID 86751885, compound

HRID 725936Notes

Reaction equation

HRID 725936 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@@H:7]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=3)=[O:34])=[CH:27][CH:26]=2)[CH2:6]1)(=O)C.[OH-].[Na+].Cl>O1CCCC1CO>[SH:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[O:11])[C@H:7]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=3)=[O:34])=[CH:27][CH:26]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86751886HCID 86751886, compound

Product 1

HCID 86751885HCID 86751885, compound

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

To a solution of (2S,4S)-4-acetylthio-N-(p-nitrobenzyloxycarbonyl)-2-[4-[N-(p-nitrobenzyloxycarbonyl)aminomethyl]phenethyl]pyrrolidine (495 mg, 0.777 mmol) in tetrahydrofuran-methanol (2:1, 15 ml), 1N aqueous sodium hydroxide (1.5 ml, 1.5 mmol) was added in a nitrogen stream under cooling with ice. After this reaction solution was stirred at the same temperature for 2 hours, 1N aqueous hydrochloric acid (2.0 ml, 2.0 mmol) was added thereto, and this mixed solution was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off in vacuo to give a crude product of (2R,4S)-4-mercapto-N-(p-nitrobenzyloxycarbonyl)-2-[4-[N-(p-nitrobenzyloxycarbonyl)aminomethyl]phenethyl]-pyrrolidine.

Workup

  1. temperatureunder cooling with ice
  2. extractionthis mixed solution was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-a4b8117fd4f848e8b6b9740b606885c5
Source dataset
uspto-grants-1998_01
Patent number
US05707987

Reaction notes

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