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

HRID 582607노트

반응식

HRID 582607 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-353101ceb0a6455cae4cbb69cc7981f3
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05925662

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