Water → Cbz-Phe-CN

HRID 539508Notes

Reaction equation

HRID 539508 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10](N)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:23]1C(Cl)=NC(Cl)=N[C:24]=1Cl.O.C(OCC)(=O)C>CN(C=O)C>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([C:24]#[N:23])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7954Cyanuric chlorideHCID 8857Ethyl AcetateHCID 2755911(S)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate

Product 1

HCID 131731969Cbz-Phe-CNYield 139.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cbz-Phe-NH2 (4.86 g, 16.29 mmoles) was dissolved in DMF under nitrogen and cooled on ice bath. Cyanuric chloride (1.95 g, 10.59 mmoles) was added with stirring, and the mixture was allowed to warm to rt overnight. Water (100 ml) and ethyl acetate (250 ml) were added to the mixture. The organic phase was separated and washed three times with water (100 ml) and then dried over magnesium sulfate. The material was filtered and concentrated in vacuo to afford Cbz-Phe-CN as a white solid (4.56 g, 99%) HPLC analysis: >99% purity; Retention time 10.1 min.

Workup

  1. temperaturecooled on ice bath
  2. customThe organic phase was separated
  3. washwashed three times with water (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe material was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d5169b79c0c4c53accac661f09a9066
Source dataset
uspto-grants-2014_10
Patent number
US08871720B2

Reaction notes

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