Hydrochloric Acid → HCID 86751883, compound

HRID 725935Notes

Reaction equation

HRID 725935 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][O: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][O:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]3[CH:38]=[CH:39][C:40]([N+:43]([O-:45])=[O:44])=[CH:41][CH:42]=3)=[O:34])=[CH:27][CH:26]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86751884HCID 86751884, compound

Product 1

HCID 86751883HCID 86751883, 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]phenoxymethyl]-pyrrolidine (786 mg, 1.23 mmol) in tetrahydrofuranmethanol (1:1, 20 ml), 1N aqueous sodium hydroxide (1.48 ml, 1.48 mmol) was added in a nitrogen stream under cooling with ice. The reaction solution was stirred at 2 hours, and 1N hydrochloric acid (1.6 ml, 1.6 mmol) was added thereto. The resulting mixed solution was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off in vacuo to obtain a crude product of (2S,4S)-4-mercapto-N-(p-nitrobenzyloxycarbonyl)-2-[4-[N-(p-nitrobenzyloxycarbonyl)aminomethyl]phenoxymethyl]-pyrrolidine.

Workup

  1. temperatureunder cooling with ice
  2. additionThe resulting mixed solution
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-d0ab740b40084e6980028024f7279a68
Source dataset
uspto-grants-1998_01
Patent number
US05707987

Reaction notes

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