Hydrochloric Acid → 2-Methyl-4-(S)-Phenyl-(L)-Proline Methyl Ester

HRID 496235Notes

Reaction equation

HRID 496235 reaction equation
C([N:8]1[CH2:16][C@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][C@@:9]1([CH3:23])[C:10]([O:12][CH3:13])=[O:11])(OC(C)(C)C)=O.Cl>CO>[CH3:13][O:12][C:10](=[O:11])[C@:9]1([CH3:23])[CH2:14][C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:16][NH:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 131725143N-BOC-2-methyl-4-(S)-phenyl-(L)-proline, methyl ester

Product 1

HCID 865924792-Methyl-4-(S)-Phenyl-(L)-Proline Methyl Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-BOC-2-methyl-4-(S)-phenyl-(L)-proline, methyl ester from Step B (1.85 g, 5.8 mmol) in MeOH was bubbled HCl (g) over a 10 min period. The HCl saturated solution was allowed to stir at rt for 5 h, concentrated in vacuo and azeotroped with toluene. The crude product was used in the subsequent step.

Workup

  1. concentrationconcentrated in vacuo
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-94ef31ecafe043e88be4cefc01edbc9a
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

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