Benzyl chloroformate → HCID 10779036, compound

HRID 2050185Notes

Reaction equation

HRID 2050185 reaction equation
[OH:1][CH:2]([CH:6]1[CH2:10][CH2:9][CH2:8][NH:7]1)[C:3]([OH:5])=[O:4].[OH-].[Na+].[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[OH:1][CH:2]([CH:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:21]([O:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:22])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 10725471HCID 10725471, compound

Product 1

HCID 10779036HCID 10779036, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1.002 g (6.9 mmoles) of 2-hydroxy-2-(pyrrolidin-2-yl)acetic acid in a solution of 550 mg (2 equivalents) of sodium hydroxide in 10 ml of water is added 1.18 ml (1.2 equivalents) of benzyloxycarbonyl chloride, and the mixture is stirred at room temperature for 1.5 hours, washed twice with ether, adjusted to pH 2 with 10% hydrochloric acid, and then extracted thrice with methylene chloride. The extract is washed with water, dried over sodium sulfate and evaporated under reduced pressure to yield 1.288 g of α-hydroxy-α-(1-benzyloxycarbonylpyrrolidin-2-yl)acetic acid in 70.3% yield.

Workup

  1. washwashed twice with ether
  2. extractionextracted thrice with methylene chloride
  3. washThe extract is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cbe903c4fa6a438ba74f90b162a358b0
Source dataset
uspto-grants-1980_04
Patent number
US04200628

Reaction notes

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