Hydrochloric Acid → N-(Carbobenzyloxy)-DL-proline

HRID 415246Notes

Reaction equation

HRID 415246 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([OH:8])=[O:7].O.[Na].[CH2:11]([O:18][C:19](Cl)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O>[CH2:11]([O:18][C:19]([N:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([OH:8])=[O:7])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 614proline dl-formHCID 10387Benzyl chloroformateHCID 71353970Sodium monohydrate

Product 1

HCID 232388N-(Carbobenzyloxy)-DL-proline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of pyrrolidine-2-carboxylic acid (1.15 g, 10 mmol) of water (20 ml) was added sodium hydrate (1.6 g, 40 mmol). Then benzyloxycarbonyl chloride (2.02 g, 12 mmol) was added drop wise at 0° C. The mixture was stirred at 0° C. for 2 h. The resulting mixture was treated with 5N hydrochloric acid to pH=6 and extracted with ethyl acetate, the solvent was removed under reduced pressure and dried in vacuum. 2.0 g of 1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe solvent was removed under reduced pressure
  3. customdried in vacuum

Sources & evidence

ORD record
ord-698f80b160d844339d272a8b57922549
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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