Benzyl chloroformate → N-[2-(ethoxycarbonyl)butyl]-N-benzyloxycarbonylalanine

HRID 1180212Notes

Reaction equation

HRID 1180212 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([CH2:14][CH3:15])[CH2:7][NH:8][C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>CC(C)=O.O>[CH2:1]([O:3][C:4]([CH:6]([CH2:14][CH3:15])[CH2:7][N:8]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 86598455N-[2-(ethoxycarbonyl)butyl]alanine

Product 1

HCID 69194551N-[2-(ethoxycarbonyl)butyl]-N-benzyloxycarbonylalanine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a suspension of N-[2-(ethoxycarbonyl)butyl]alanine (2.2 g, 10 mmol) and potassium carbonate (2.2 g, 16 mmol) in a mixture of acetone (30 mL) and water (2.5 mL) was added benzyl chloroformate (2.0 mL, 2.4 g, 14 mmol) at 0-5° C. After stirring for 2 h at ambient temperature the solid was filtered off, the solvent was evaporated, the residue was stirred with cold aqueous sodium hydroxide solution [prepared from ice (20 g) and aqueous sodium hydroxide solution (1N, 40 mL)] and extracted with ethyl acetate (40 mL). The aqueous layer was acidified with an aqueous solution of hydrochloric acid 1/1 (20 mL) and the mixture was extracted with ethyl acetate (40 mL). After drying and evaporation N-[2-(ethoxycarbonyl)butyl]-N-benzyloxycarbonylalanine (1.66 g, 47%) was obtained as a yellow oil which can be used in the next reaction without further purification.

Workup

  1. filtrationwas filtered off
  2. customthe solvent was evaporated
  3. stirringthe residue was stirred with cold aqueous sodium hydroxide solution [prepared from ice (20 g) and aqueous sodium hydroxide solution (1N, 40 mL)]
  4. extractionextracted with ethyl acetate (40 mL)
  5. extractionthe mixture was extracted with ethyl acetate (40 mL)
  6. customAfter drying
  7. customevaporation N-[2-(ethoxycarbonyl)butyl]-N-benzyloxycarbonylalanine (1.66 g, 47%)
  8. customwas obtained as a yellow oil which
  9. customcan be used in the next reaction without further purification

Sources & evidence

ORD record
ord-5d288f3bc0974eb8ae977141825b3b8e
Source dataset
uspto-grants-2007_10
Patent number
US07279595B2

Reaction notes

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