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

HRID 2259654노트

반응식

HRID 2259654 반응식
[OH:1][C@H:2]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([N:17]3[CH2:21][C@H:20]([CH2:22][O:23][CH3:24])[O:19][C:18]3=[O:25])[CH:14]=[CH:13][C:11]=2[N:12]=1)[CH2:3][CH2:4][C:5](=O)[NH2:6].O1CCOCC1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[OH:1][C@H:2]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([N:17]3[CH2:21][C@H:20]([CH2:22][O:23][CH3:24])[O:19][C:18]3=[O:25])[CH:14]=[CH:13][C:11]=2[N:12]=1)[CH2:3][CH2:4][C:5]#[N:6]

참가 물질

6

반응물 4

HCID 9845Trifluoroacetic anhydrideHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 15342518HCID 15342518, 화합물

생성물 1

HCID 98846473[2-(1(S)-Hydroxy-3-cyanopropyl)benzothiazol-6-yl]-5(R)-methoxymethyl-2-oxazolidinone수율 84.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

2.0 g of 3-[2-(1(S)-hydroxy-3-carbamoylpropyl)benzothiazol-6-yl]-5(R)-methoxymethyl-2-oxazolidinone was suspended in a liquid mixture of 20 ml of 1,4-dioxane and 3.6 ml of pyridine. 2.0 ml of trifluoroacetic anhydride was added dropwise thereto under cooling with ice for 20 min. The resulting mixture was stirred at room temperature for 2 h and the reaction liquid was added to a saturated aqueous sodium hydrogencarbonate solution. After extraction with ethyl acetate, the organic layer was washed with dilute hydrochloric acid and then with a saturated aqueous common salt solution, and dried. The solvent was distilled off and the resulting residue was crystallized from acetone/water to give 1.6 g of the titled compound.

후처리

  1. temperatureunder cooling with ice for 20 min
  2. customthe reaction liquid
  3. extractionAfter extraction with ethyl acetate
  4. washthe organic layer was washed with dilute hydrochloric acid
  5. customwith a saturated aqueous common salt solution, and dried
  6. distillationThe solvent was distilled off
  7. customthe resulting residue was crystallized from acetone/water

출처 및 근거

ORD 기록
ord-e36e6b85220c41af94ff160207363755
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05475014

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