Acetic Anhydride → 2-((N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)acetamido)methyl)phenyl acetate

HRID 1048341Notes

Reaction equation

HRID 1048341 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH:26]=[CH2:27])[C@H:9]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[OH:25])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:35](OC(=O)C)(=[O:37])[CH3:36].[C:42](OCC)(=[O:44])[CH3:43]>C1COCC1.C(Cl)Cl>[C:35]([O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:17]([C@H:9]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C@@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH:26]=[CH2:27])[C:42](=[O:44])[CH3:43])(=[O:37])[CH3:36]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 585734252-(((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enylamino)methyl)phenol

Product 1

HCID 585738512-((N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)acetamido)methyl)phenyl acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.1 g (2.76 mmol) of 2-(((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enylamino)methyl)phenol (Example 115, Step B) and triethylamine (0.85 mL, 6.08 mmol) in a mixture of THF (5.0 mL) and DCM (5.0 mL) was added acetic anhydride (0.55 mL, 5.80 mmol) at 0° C. The temperature of the reaction was slowly allowed to rise to room temperature and the mixture was stirred at ambient temperature overnight. When LCMS indicated completion of the reaction, 100 ml of ethyl acetate was added and the combined organics were washed consecutively with water (30 ml), citric acid (30 ml, 1M), NaHCO3 solution (30 ml) and sat. NaCl solution (30 ml), dried over MgSO4, filtered and the filtrate was concentrated to give the title compound. The crude product was used without further purification.

Workup

  1. customto rise to room temperature
  2. additionwas added
  3. washthe combined organics were washed consecutively with water (30 ml), citric acid (30 ml, 1M), NaHCO3 solution (30 ml) and sat. NaCl solution (30 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-97ae444afaea4bd1909c0ac2181de935
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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