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

HRID 495445ノート

反応式

HRID 495445 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-526d6ff1fb4f4497862e3ba23d2ff120
出典データセット
uspto-grants-2005_09
特許番号
US06939871B2

反応ノート

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