Benzyl chloroformate → N-Cbz-d-alanine

HRID 437330Notes

Reaction equation

HRID 437330 reaction equation
[NH2:1][C@@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[CH2:7]([O:14][C:15](Cl)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>>[CH2:7]([O:14][C:15]([NH:1][C@@H:2]([C:4]([OH:6])=[O:5])[CH3:3])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide3×HCID 71080D-Alanine2×

Product 1

HCID 70832N-Cbz-d-alanine

Procedure

D-alanine is reacted (12.5 g., 0.14 mol) with 26 g., 0.14 mol + 2 g. excess. of benzyloxycarbonyl chloride and 0.28 mol of sodium hydroxide. The D-alanine is dissolved in one equivalent of sodium hydroxide solution, cooled in ice, and treated slowly with the acid chloride and the second equivalent of sodium hydroxide while maintaining pH 10-12. The reaction is stirred for an additional hour with cooling and is worked up by extraction with ether and acidification of the aqueous solution. A precipitate soon solidifies and is collected and dried; 23.5 g.; m.p. 82°-85° C.

Workup

  1. temperaturecooled in ice
  2. temperaturewith cooling
  3. extractionis worked up by extraction with ether and acidification of the aqueous solution
  4. customis collected
  5. customdried

Sources & evidence

ORD record
ord-92e15e960dce4218a6e8b979fad0b11c
Source dataset
uspto-grants-1977_06
Patent number
US04031071

Reaction notes

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