1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → N-t-butoxycarbonyl-(S)-proline phenylcarbamoylmethyl ester

HRID 476987

Reaction equation

HRID 476987 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]1([NH:22][C:23]([CH2:25]Br)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[C:16]1([NH:22][C:23]([CH2:25][O:11][C:10](=[O:12])[C@@H:9]2[CH2:13][CH2:14][CH2:15][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 948182-Bromo-N-phenylacetamideHCID 516892Sodium Bicarbonate

Product 1

HCID 15598553N-t-butoxycarbonyl-(S)-proline phenylcarbamoylmethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 15 ml of DMF were dissolved 2.8 g of N-t-butoxycarbonyl-(S)-proline and 2.8 g of phenylcarbamoyl methyl bromide. To the solution was added 1.1 g of sodium hydrogencarbonate. The mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (using chloroform as an eluent), giving the title compound as a colorless oil. Yield 3.5 g.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-49a9a423294f48a0bdff64fa41949f5d
Source dataset
uspto-grants-1989_12
Patent number
US04886813

Linked notes

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