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

HRID 2296700ノート

反応式

HRID 2296700 の反応式
[Br:1][CH2:2][CH2:3][CH:4]1[O:10][C:9]([C:15]#[C: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]([C:15]#[C: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]

参加物

4

反応物 2

HCID 962WaterHCID 183873763-(2-Bromoethyl)-7-chloro-5-cyclopropylethynyl-1,5-dihydro-1-(4-methoxybenzyl)-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

生成物 1

HCID 57189482rel-(3S,5S)-3-(2-Bromoethyl)-7-chloro-5-cyclopropylethynyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a room temperature solution of 1.13 g of 3-(2-bromoethyl)-7-chloro-5-cyclopropylethynyl-1,5-dihydro-1-(4-methoxybenzyl)-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one in 50 mL of acetonitrile was added 25 mL of water and 5.7 g of ceric ammonium nitrate. After 30 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 (270 mg) was the title compound.

後処理

  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 (270 mg)

出典と根拠

ORDレコード
ord-1e6ff7103a844e28b5531def43b1b0ae
出典データセット
uspto-grants-2002_12
特許番号
US06489320B1

反応ノート

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