Hydrochloric Acid → HCID 86751887, compound

HRID 725937Notes

Reaction equation

HRID 725937 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][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([CH2:34][NH:35][C:36]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=3)=[O:37])=[CH:26][CH:25]=2)[CH2:6]1)(=O)C.[OH-].[Na+].Cl>CO.O1CCCC1>[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][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([CH2:34][NH:35][C:36]([O:38][CH2:39][C:40]3[CH:41]=[CH:42][C:43]([N+:46]([O-:48])=[O:47])=[CH:44][CH:45]=3)=[O:37])=[CH:26][CH:25]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86751888HCID 86751888, compound

Product 1

HCID 86751887HCID 86751887, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (2R,4S)-4-acetylthio-N-(p-nitrobenzyloxycarbonyl)-2-[4-(p-nitrobenzyloxycarbonylaminomethyl)-1-naphthylmethyl]pyrrolidine (144 mg, 0.21 mmol) in methanol-tetrahydrofuran (3:1) (4 ml), 1N aqueous sodium hydroxide (0.24 ml, 0.24 mmol) was added in a nitrogen stream under cooling with ice. This reaction solution was stirred for 10 minutes and then 1N hydrochloric acid (0.24 ml, 0.24 mmol) was added thereto. Then the resulting solution was concentrated in vacuo. The resulting residue was poured into a liquid mixture of ethyl acetate with water. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated in vacuo to give a crude product of (2R,4S)-4-mercapto-N-(p-nitrobenzyloxycarbonyl)-2-[4-(p-nitrobenzyloxycarbonylaminomethyl)-1-naphthylmethyl]-pyrrolidine as a yellow oily substance.

Workup

  1. temperatureunder cooling with ice
  2. concentrationThen the resulting solution was concentrated in vacuo
  3. additionThe resulting residue was poured into a liquid mixture of ethyl acetate with water
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-138f0a9fe8e94730a8cb1872e2e4338c
Source dataset
uspto-grants-1998_01
Patent number
US05707987

Reaction notes

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