Benzyl chloroformate → (2S)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

HRID 1087627Notes

Reaction equation

HRID 1087627 reaction equation
[OH:1][CH:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.C(=O)(O)[O-].[Na+].[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[C:23]([N:5]1[CH2:6][CH:2]([OH:1])[CH2:3][C@H:4]1[C:7]([OH:9])=[O:8])([O:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:24]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 69248L-Proline, 4-hydroxy-, cis-HCID 516892Sodium Bicarbonate

Product 1

HCID 12731799(2S)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 20 g (152.5 mmol) of 4-hydroxy-L-proline in 35 ml of water was added 36.7 g (436.8 mmol) of sodium bicarbonate and the mixture was cooled to 10° C. before 32.5 g (190.5 mmol) of benzylchloroformate wa added dropwise. The cooling bath was then removed and the mixture was allowed to stir for 24 hours at room temperature. The pH of the reaction was then adjusted to 1 with concentrated HC1 solution and the mixture was extracted with 3 x 100 ml portions of methylene chloride. The organic layers were dried over Na2SO4 and evaporated in vacuum to provide 36.4 g of the product as an oil (90% yield). NMR(CDC13): 7.30 (m,5H, aromatic), 5.12 (m,2H), 4.50 (m,2H), 4.36 (m,2H), 3.6 (m,2H), 2.38 (m,2H).

Workup

  1. additionwa added dropwise
  2. customThe cooling bath was then removed
  3. extractionthe mixture was extracted with 3 x 100 ml portions of methylene chloride
  4. dry with materialThe organic layers were dried over Na2SO4
  5. customevaporated in vacuum

Sources & evidence

ORD record
ord-b2c0179a98bf4c629d14fa29ae98472d
Source dataset
uspto-grants-1991_07
Patent number
US05036153

Reaction notes

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