Water → rel-(3S,5S)-trans-3-(2-Bromoethyl)-7-chloro-5-cyclopropylethenyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2 (3H)-one

HRID 2296702노트

반응식

HRID 2296702 반응식
[Br:1][CH2:2][CH2:3][CH:4]1[O:10][C:9](/[CH:15]=[CH:16]/[CH:17]2[CH2:19][CH2:18]2)([C:11]([F:14])([F:13])[F:12])[C:8]2[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:7]=2[N:6](CC2C=CC(OC)=CC=2)[C:5]1=[O:34].O>C(#N)C>[Br:1][CH2:2][CH2:3][C@@H:4]1[O:10][C@:9](/[CH:15]=[CH:16]/[CH:17]2[CH2:18][CH2:19]2)([C:11]([F:13])([F:14])[F:12])[C:8]2[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:7]=2[NH:6][C:5]1=[O:34]

참가 물질

4

반응물 2

HCID 962WaterHCID 18387384trans-3-(2bromoethyl)-7-chloro-5-cyclopropylethenyl-1,5-dihydro-l-(4-methoxybenzyl)-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

생성물 1

HCID 86755964rel-(3S,5S)-trans-3-(2-Bromoethyl)-7-chloro-5-cyclopropylethenyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2 (3H)-one

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a room temperature solution of 750 mg of trans-3-(2bromoethyl)-7-chloro-5-cyclopropylethenyl-1,5-dihydro-l-(4-methoxybenzyl)-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one in 35 mL of acetonitrile was added 18 mL of water and 3.78 g of ceric ammonium nitrate. After 20 min, the reaction mixture was partitioned between water and ether, and the organic layer was washed with aqueous bicarbonate and brine, dried and evaporated. This produced two diastereomeric products which were separated by column chromatography over silica gel (elution with 10-25% ethyl acetate in hexanes). The first diastereomer eluted (162 mg) was the title compound.

후처리

  1. customthe reaction mixture was partitioned between water and ether
  2. washthe organic layer was washed with aqueous bicarbonate and brine
  3. customdried
  4. customevaporated
  5. customThis produced two diastereomeric products which
  6. customwere separated by column chromatography over silica gel (elution with 10-25% ethyl acetate in hexanes)
  7. washThe first diastereomer eluted (162 mg)

출처 및 근거

ORD 기록
ord-bc82a45a3e7249589e2f723d5eecf04b
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06489320B1

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