Acetic Anhydride → HCID 178475439, compound

HRID 480964Notes

Reaction equation

HRID 480964 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C@@:16]([OH:48])([CH2:42][N:43]1[CH:47]=[N:46][CH:45]=[N:44]1)[C@H:17]([S:19][C@@H:20]1[CH2:25][O:24][C@@H:23]([C:26]2[CH:41]=[CH:40][C:29]([C:30]([NH:32][C:33]3[CH:38]=CC(O)=[CH:35][CH:34]=3)=[O:31])=[CH:28][CH:27]=2)[O:22][CH2:21]1)[CH3:18].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:5]([O:4][C:1]1[CH:35]=[CH:34][C:33]([NH:32][C:30](=[O:31])[C:29]2[CH:28]=[CH:27][C:26]([C@H:23]3[O:22][CH2:21][C@H:20]([S:19][C@H:17]([CH3:18])[C@:16]([C:10]4[CH:11]=[CH:12][C:13]([F:15])=[CH:14][C:9]=4[F:8])([OH:48])[CH2:42][N:43]4[CH:47]=[N:46][CH:45]=[N:44]4)[CH2:25][O:24]3)=[CH:41][CH:40]=2)=[CH:38][CH:2]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178462401HCID 178462401, compound

Product 1

HCID 178475439HCID 178475439, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Acetic anhydride (1.5 ml) was added dropwise to a solution of 4-[trans-5-[[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]thio]-1,3-dioxan-2-yl]-4′-hydroxybenzanilide (40 mg, 0.07 mmol), obtained in Example 23(2), in anhydrous pyridine (3 ml) cooled to 0° C. with stirring. The resulting mixture was stirred at room temperature overnight. At the end of this time, the reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution at 0° C. The resulting mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the title compound (43 mg, yield 100%) as a colorless oil. The oil was recrystallized from ethyl acetate-hexane to give white powdery crystals.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customThe resulting mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e4dd60051214c2bac0a03f27713e639
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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