Sodium Bicarbonate → 3[2-(1(S)-Hydroxy-3-cyanopropyl)benzothiazol-6-yl]-5(R)-methoxymethyl-2-oxazolidinone

HRID 2259652노트

반응식

HRID 2259652 반응식
[OH:1][CH:2]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N:16]3[CH2:20][CH:19]([CH2:21][O:22][CH3:23])[O:18][C:17]3=[O:24])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:3][CH:4]=NO.FC(F)(F)C([C:29]1[NH:30]C=CN=1)=O.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:1][C@H:2]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N:16]3[CH2:20][C@H:19]([CH2:21][O:22][CH3:23])[O:18][C:17]3=[O:24])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:3][CH2:4][C:29]#[N:30]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 5654362,2,2-Trifluoro-1-(1H-imidazol-2-yl)ethanoneHCID 73508098HCID 73508098, 화합물

생성물 1

HCID 98846473[2-(1(S)-Hydroxy-3-cyanopropyl)benzothiazol-6-yl]-5(R)-methoxymethyl-2-oxazolidinone수율 70.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

73 g of the 3-[2-(1-hydroxy-3-hydroxyiminopropyl)benzothiazol-6-yl]-5-methoxymethyl-2 -oxazolidinone obtained in the Example 8 was dissolved in 800 ml of tetrahydrofuran. 90 g of trifluoroacetylimidazole was added dropwise to the solution under cooling with ice and the mixture was stirred at room temperature for 4 h. The reaction liquid was poured into an aqueous sodium hydrogencarbonate solution. After extraction with ethyl acetate followed by washing with an aqueous common salt solution, drying over magnesium sulfate and concentration under reduced pressure, the obtained solid was recrystallized from acetone/water to give 51 g of the titled compound.

후처리

  1. temperatureunder cooling with ice
  2. customThe reaction liquid
  3. extractionAfter extraction with ethyl acetate
  4. washby washing with an aqueous common salt solution
  5. dry with materialdrying over magnesium sulfate and concentration under reduced pressure
  6. customthe obtained solid was recrystallized from acetone/water

출처 및 근거

ORD 기록
ord-504c034ea2b04ddcaeb496797fa0a37c
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05475014

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