Diethyl Ether → (R)-2-(((Benzyloxy)carbonyl)amino)-3-mercapto-3-methylbutanoic acid

HRID 861337

Reaction equation

HRID 861337 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].[OH-].[K+].CCOCC.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>O>[CH2:21]([O:20][C:18]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10387Benzyl chloroformateHCID 14797Potassium HydroxideHCID 92863L-Penicillamine

Product 1

HCID 22881903(R)-2-(((Benzyloxy)carbonyl)amino)-3-mercapto-3-methylbutanoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To L-penicillamine (15.75 g; 105.8 mmol) was added a solution of KOH (12.4 g; 222.2 mmol) in water (250 ml). When the solution was complete, Et2O (100 ml) was added and the solution cooled to 0° C. Benzyl chloroformate (14.9 ml; 105.8 mmol) was added dropwise and the stirred reaction mixture allowed to warm to RT. The layers were separated, the aqueous layer acidified to pH 1-1.5 with 1N hydrochloric acid, extracted with CH2Cl2 (×3) and dried (MgSO4). The solvent was removed in vacuo to yield N-benzyloxycarbonyl-L-penicillamine (21.27 g).

Workup

  1. customthe stirred reaction mixture
  2. temperatureto warm to RT
  3. customThe layers were separated
  4. extractionextracted with CH2Cl2 (×3)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0c88967e6cef41ed979b3bca0ed3d417
Source dataset
uspto-grants-1998_02
Patent number
US05714491

Linked notes

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