Potassium Carbonate → 3-[2-(2-Phenylmethoxy-3,3,3-trifluoropropyl)-3,4-dihydro-2H-1-benzopyran-6-yl]-5(R)-methoxymethyloxazolidin-2-one

HRID 582607Notes

Reaction equation

HRID 582607 reaction equation
[C:1]1([CH2:7][O:8][CH:9]([C:27]([F:30])([F:29])[F:28])[CH2:10][CH:11]2[CH2:16][CH2:15][C:14]3[CH:17]=[C:18]([NH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:19]=[CH:20][C:13]=3[O:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:37][O:38][CH2:39][C@H]1COC(=O)O1>CN(C)C=O.O>[C:1]1([CH2:7][O:8][CH:9]([C:27]([F:30])([F:28])[F:29])[CH2:10][CH:11]2[CH2:16][CH2:15][C:14]3[CH:17]=[C:18]([N:21]4[CH2:26][C@H:25]([CH2:37][O:38][CH3:39])[O:24][C:22]4=[O:23])[CH:19]=[CH:20][C:13]=3[O:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 110043812-(2-Phenylmethoxy-3,3,3-trifluoropropyl)-6-ethoxycarbonylamino-3,4-dihydro-2H-1-benzopyranHCID 11007941(S)-(-)-4-(Methoxymethyl)-1,3-dioxolan-2-one

Product 1

HCID 110051173-[2-(2-Phenylmethoxy-3,3,3-trifluoropropyl)-3,4-dihydro-2H-1-benzopyran-6-yl]-5(R)-methoxymethyloxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4.2 g (9.9 mmol) of 2-(2-phenylmethoxy-3,3,3-trifluoropropyl)-6-ethoxycarbonylamino-3,4-dihydro-2H-1-benzopyran in 40 ml of dimethylformamide is stirred for 24 hours, at 130° C., in the presence of 140 mg (1.0 mmol) of potassium carbonate and of 3.4 g (26 mmol) of 4(S)-methoxymethyl-1,3-dioxolan-2-one added in 3 hours. The mixture is cooled, diluted with water and the product is extracted with diethyl ether. The organic phase is then dried over sodium sulfate, concentrated under reduced pressure and chromatographed on a silica column using a 30/70 mixture of ethyl acetate and cyclohexane. The product obtained is used as such in the following step.

Workup

  1. additionadded in 3 hours
  2. temperatureThe mixture is cooled
  3. extractionthe product is extracted with diethyl ether
  4. dry with materialThe organic phase is then dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on a silica column
  7. additiona 30/70 mixture of ethyl acetate and cyclohexane
  8. customThe product obtained

Sources & evidence

ORD record
ord-353101ceb0a6455cae4cbb69cc7981f3
Source dataset
uspto-grants-1999_07
Patent number
US05925662

Reaction notes

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