Chloroacetonitrile → HCID 59909941, compound

HRID 2116999Notes

Reaction equation

HRID 2116999 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[C@H:10]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:35][C:36]#[N:37]>CC(C)=O>[CH2:1]([O:8][C:9](=[O:27])[C@@H:10]([NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:35][C:36]#[N:37])=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 10796Cesium carbonateHCID 7019055Boc-L-tyrosine benzyl ester

Product 1

HCID 59909941HCID 59909941, compoundYield 109.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-Boc-L-tyrosine benzyl ester (0.371 g, 1 mmol) was dissolved in acetone (5 mL) and cesium carbonate (0.650 g, 2 mmol) was added followed by chloroacetonitrile (0.150 g, 2 mmol). The mixture was then reflux for 2 h. The reaction was cooled to room temperature and insoluble salts removed by filtration using acetone for washings. Volatiles were removed under reduced pressure and the residue dissolved in DCM. The solution was washed with brine, dried (MgSO4) and concentrated to give the desired product as an oil (450 mg).

Workup

  1. temperatureThe mixture was then reflux for 2 h
  2. custominsoluble salts removed by filtration
  3. customVolatiles were removed under reduced pressure
  4. dissolutionthe residue dissolved in DCM
  5. washThe solution was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-27b60d12ab004bd3a5612be944912212
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Reaction notes

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