Acetyl chloride → HCID 21905107, compound

HRID 1247327Notes

Reaction equation

HRID 1247327 reaction equation
[NH2:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)=[O:4].C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29]>ClCCl>[C:28]([NH:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)=[O:4])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21905108HCID 21905108, compound

Product 1

HCID 21905107HCID 21905107, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (RS)-2-amino-N-(4-cyano-benzyl)-2-phenyl-acetamide (0.1 g) in dichloromethane (5 ml) was cooled to 0° C. and treated with triethylamine (58 μl) and acetyl chloride (28 μl). The reaction mixture was stirred at rt for 1 hr, then diluted with dichloromethane, washed with 1N HCl and brine. The organic layer was dried over MgSO4, filtered and concentrated. The product was isolated by chromatography (silica gel, gradient dichloromethane=>dichloromethane/MeOH 9:1) to give (RS)-2-acetylamino-N-(4-cyano-benzyl)-2-phenyl-acetamide (98 mg). Off-white solid. MS 308.2 ([M+H]+)

Workup

  1. washwashed with 1N HCl and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was isolated by chromatography (silica gel, gradient dichloromethane=>dichloromethane/MeOH 9:1)

Sources & evidence

ORD record
ord-c21feb9ad9e14336904dcea2eb45435b
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

Loading…