Hydrochloric Acid → HCID 56977651, compound

HRID 1195660Notes

Reaction equation

HRID 1195660 reaction equation
[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([C@@H:24]2[CH2:26][C@H:25]2[C:27]([O:29]CC)=[O:28])[CH2:7]1)(=[O:4])=[O:3].[Li+].[OH-].Cl>CO>[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)=[O:12])[C@H:8]([C@@H:24]2[CH2:26][C@H:25]2[C:27]([OH:29])=[O:28])[CH2:7]1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57084124HCID 57084124, compound

Product 1

HCID 56977651HCID 56977651, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of ethyl trans-2-[(2S, 4R)-4-methanesulfonyloxy-N-(4-nitrobenzyloxycarbonyl) pyrrolidin-2-yl]cyclopropanecarboxylate (750 mg, 1.64 mmol) and MeOH (15 ml) was treated with 2N LiOH (2.4 ml, 4.8 mmol) at room temperature over 12 hours. The reaction mixture was neutralized with 6N HCl (0.80 ml, 4.8 mmol) and extracted with CH2Cl2 (20 ml×2). The organic layers were combined, dried (MgSO4) and concentrated to afford trans-2-[(2S, 4R)-4-methanesulfonyloxy-N-(4-nitrobenzyloxycarbonyl)pyrrolidin-2yl]cyclopropanecarboxylic acid (565 mg, 80% yield) as a residue.

Workup

  1. extractionextracted with CH2Cl2 (20 ml×2)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d1cdfe008bfa4ffa94fd2ce8d13664d7
Source dataset
uspto-grants-1992_05
Patent number
US05112818

Reaction notes

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