Triethylamine → 7,8-Difluoro-6-hydroxymethyl-4h-benzo[1,4]oxazin-3-one

HRID 495445노트

반응식

HRID 495445 반응식
C(N(CC)CC)C.[F:8][C:9]1[C:19]([C:20](O)=[O:21])=[CH:18][C:12]2[NH:13][C:14](=[O:17])[CH2:15][O:16][C:11]=2[C:10]=1[F:23].ClC(OCC(C)C)=O>C1COCC1>[F:8][C:9]1[C:19]([CH2:20][OH:21])=[CH:18][C:12]2[NH:13][C:14](=[O:17])[CH2:15][O:16][C:11]=2[C:10]=1[F:23]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 223266397,8-Difluoro-4h-benzo[1,4]oxazine-3-one-6-carboxylic acid

생성물 1

HCID 223267117,8-Difluoro-6-hydroxymethyl-4h-benzo[1,4]oxazin-3-one수율 34%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (2.4 mL, 17.3 mmol) was added to a suspension of 7,8-difluoro-4H-benzo[1,4]oxazine-3-one-6-carboxylic acid (3.6 g, 15.7 mmol) in anhydrous THF (250 mL). Isobutyl chloroformate (2.2 mL, 17.3 mmol) was added to the mixture at ice cold temperature over 0.5 hour. Stirring was continued for further 2 hours at room temperature. It was then cooled in ice and the solid was removed by filtration. The filtrate was added to a cold solution of sodium borohydride (3.2 g) in water. The mixture was stirred in cold for 1 hour before it was concentrated in vacuo to half and acidified with 2M hydrochloric acid. The resulting solid precipitate was collected by filtration and dried to give the title compound (1.15 g, 22%).

후처리

  1. temperatureIt was then cooled in ice
  2. customthe solid was removed by filtration
  3. additionThe filtrate was added to a cold solution of sodium borohydride (3.2 g) in water
  4. stirringThe mixture was stirred in cold for 1 hour before it
  5. concentrationwas concentrated in vacuo to half
  6. filtrationThe resulting solid precipitate was collected by filtration
  7. customdried

출처 및 근거

ORD 기록
ord-526d6ff1fb4f4497862e3ba23d2ff120
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939871B2

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