Acetic Anhydride → (2S)-2-{[(Benzyloxy)carbonyl]amino}-3-cyanopropanoic acid

HRID 1578058Notes

Reaction equation

HRID 1578058 reaction equation
[C:1]([NH:11][C@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14](=O)[NH2:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:1]([NH:11][C@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14]#[N:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 75314Benzyloxycarbonyl-asparagine

Product 1

HCID 12771373(2S)-2-{[(Benzyloxy)carbonyl]amino}-3-cyanopropanoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.66 g (10 millimole) of N-carbobenzoxy-L-asparagine (Journal of Organic Chemistry, 26, 3356-3360 (1961)) was admixed with 30 ml of dry pyridine and 1.2 ml (12 millimole) of acetic anhydride, and the admixture obtained was stirred at a temperature from 20° to 25° C. for one hour. The reaction solution was then concentrated to a syrup by distilling off pyridine under reduced pressure, and the residue was diluted with 50 ml of 1 N hydrochloric acid. The product deposited as colorless needles was collected by filtration, washed with cold water and dried to afford 2.05 g of N-carbobenzoxy-β-cyano-L-alanine. Yield 83%. This product was found to have the following properties:

Workup

  1. customthe admixture obtained
  2. concentrationThe reaction solution was then concentrated to a syrup
  3. distillationby distilling off pyridine under reduced pressure
  4. additionthe residue was diluted with 50 ml of 1 N hydrochloric acid
  5. filtrationwas collected by filtration
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-fc8de43eb9c9417c8d4165ecb7dd6739
Source dataset
uspto-grants-1981_09
Patent number
US04290972

Reaction notes

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