2-Nitrophenyl selenocyanate → rel-(3S,5S)-7-Chloro-5-(2-cyclopropylethynyl)-1,5-dihydro-3-ethen yl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

HRID 2296701노트

반응식

HRID 2296701 반응식
[N+](C1C=CC=CC=1[Se]C#N)([O-])=O.[BH4-].[Na+].Br[CH2:16][CH2:17][C@@H:18]1[O:24][C@:23]([C:29]#[C:30][CH:31]2[CH2:33][CH2:32]2)([C:25]([F:28])([F:27])[F:26])[C:22]2[CH:34]=[C:35]([Cl:38])[CH:36]=[CH:37][C:21]=2[NH:20][C:19]1=[O:39]>C1COCC1.C(O)C>[Cl:38][C:35]1[CH:36]=[CH:37][C:21]2[NH:20][C:19](=[O:39])[C@H:18]([CH:17]=[CH2:16])[O:24][C@:23]([C:29]#[C:30][CH:31]3[CH2:33][CH2:32]3)([C:25]([F:26])([F:27])[F:28])[C:22]=2[CH:34]=1

참가 물질

6

반응물 3

HCID 1039312-Nitrophenyl selenocyanateHCID 4311764Sodium borohydrideHCID 57189482rel-(3S,5S)-3-(2-Bromoethyl)-7-chloro-5-cyclopropylethynyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

생성물 1

HCID 56994752rel-(3S,5S)-7-Chloro-5-(2-cyclopropylethynyl)-1,5-dihydro-3-ethen yl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one수율 61.4%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

To a room temperature solution of 409 mg (1.8 mmol) of 2-nitrophenylselenocyanate in 5.0 mL of THF was added 16 mL of ethanol and 90 mg of sodium borohydride. After stirring 1 h, a solution of 260 mg of rel-(3S,5S)-3-(2-Bromoethyl)-7-chloro-5-cyclopropylethynyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one in 1.5 mL of dry THF and 8 mL of ethanol was added, and the resulting mixture was stirred at ambient temperature for 2 h, at which time an additional 20 for an additional 2 h. The reaction mixture was partitioned between water and ether, and the organic layer was washed with aqueous bicarbonate and brine, dried and evaporated. The crude product was purified by column chromatography over silica gel (elution with 10-25% ethyl acetate in hexanes) to give 130 mg of the title compound as a pure solid: HRMS: Calcd. for C17H14NO2F3Cl (M+H)+: 354.0508. Found: 354.0487.

후처리

  1. stirringthe resulting mixture was stirred at ambient temperature for 2 h, at which time an additional 20 for an additional 2 h
  2. customThe reaction mixture was partitioned between water and ether
  3. washthe organic layer was washed with aqueous bicarbonate and brine
  4. customdried
  5. customevaporated
  6. customThe crude product was purified by column chromatography over silica gel (elution with 10-25% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-2bea407f22e04b39a98215a2aeec43bf
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06489320B1

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