Benzyl chloroformate → N-Cbz-D-Asparagine

HRID 2083833Notes

Reaction equation

HRID 2083833 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].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>[CH2:15]([O:22][C:23]([NH:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 439600D-AsparagineHCID 516892Sodium Bicarbonate

Product 1

HCID 1712147N-Cbz-D-Asparagine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

D-Asparagine, 50 g., is dissolved in 500 ml. of water at 60° C., adding 70 g. of sodium bicarbonate and cooling to 20° C. The solution is treated with 68 g. of benzylchloroformate during one hour with stirring and is stirred for an additional two and a half hours. The solution is extracted three times with ether and the aqueous solution is acidified with cold concentrated hydrochloric acid. The white solid product is separated, washed with water and dried; 77 g.; m.p. 165°-166° C.; [α]D23 + 7.4° (c 2.02, DMF).

Workup

  1. dissolution, is dissolved in 500 ml
  2. additionThe solution is treated with 68 g
  3. extractionThe solution is extracted three times with ether
  4. customThe white solid product is separated
  5. washwashed with water
  6. customdried
  7. custom[α]D23 + 7.4° (c 2.02, DMF)

Sources & evidence

ORD record
ord-dd10766dca32487aab8b00df13a6b510
Source dataset
uspto-grants-1978_04
Patent number
US04086219

Reaction notes

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