Hydrochloric Acid → HCID 86745769, compound

HRID 1195656Notes

Reaction equation

HRID 1195656 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]([C@@H:5]1[CH2:7][C@H:6]1[C@@H:8]1[CH2:12][C@H:11]([S:13]C(=O)C)[CH2:10][N:9]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:18])=[O:4].[OH-].[Na+].Cl.O>CO>[CH3:1][N:2]([CH3:30])[C:3]([C@@H:5]1[CH2:7][C@H:6]1[C@@H:8]1[CH2:12][C@H:11]([SH:13])[CH2:10][N:9]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:18])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86745770HCID 86745770, compound

Product 1

HCID 86745769HCID 86745769, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trans-N,N-dimethyl-2-[(2S,4S)-4-acetylthio -N-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]cyclopropanecarboxamide (220 mg, 0.5 mmol) in methanol (11 ml) was added 2N sodium hydroxide solution(0.50 ml, 1.0 mmol) under ice-cooling, and the solution stirred for 1 hour. To the reaction mixture was added 6N hydrochloric acid (0.17 ml, 1.0 mmol), and the mixture poured into water (10 ml) and extracted with methylene chloride (20 ml×2). The organic layer was dried (MgSO4) and evaporated in reduced pressure to give a residue of trans-N,N-dimethyl-2-[(2S,4S)-4-mercapto-N-(4-nitrobenzyloxycarbonyl) pyrrolidin-2-yl]cyclopropanecarboxamide. ##STR170##

Workup

  1. temperaturecooling
  2. extractionextracted with methylene chloride (20 ml×2)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated in reduced pressure

Sources & evidence

ORD record
ord-c650c333406a4d6498980cc792cdc95d
Source dataset
uspto-grants-1992_05
Patent number
US05112818

Reaction notes

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