Acetic Anhydride → HCID 67718766, compound

HRID 1106939Notes

Reaction equation

HRID 1106939 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[CH2:8]([O:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)CCO)=[O:14])[CH2:9][CH2:10][CH3:11].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:8]([O:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:26][CH2:31][C:30]1[CH:29]=[CH:28][CH:27]=[C:5]([O:4][C:1]([CH3:2])=[O:3])[CH:6]=1)=[O:14])[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18788148HCID 18788148, compound

Product 1

HCID 67718766HCID 67718766, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Acetic anhydride (0.42 ml, 0.42 mmol) was added to a solution of N-butyloxycarbonyl-2-(3-hydroxy-1-phenylpropyl)aniline (1.21 g, 3.7 mmol), triethylamine (0.77 ml, 5.56 mmol) and DMAP (5 mg) in DCM (25 ml). After stirring at room temperature for 90 minutes the reaction mixture was diluted with DCM (25 ml), washed with 10% aqueous citric acid solution (40 ml), saturated aqueous sodium bicarbonate solution (40 ml) and dried (MgSO4). Filtration and evaporation of the solvent gave the product. (1.39 g, 100%).

Workup

  1. washwashed with 10% aqueous citric acid solution (40 ml), saturated aqueous sodium bicarbonate solution (40 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationFiltration and evaporation of the solvent
  4. customgave the product

Sources & evidence

ORD record
ord-b10afecc86124e938332588847c23627
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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