Water → (S)-2-{[1-(4-Chloro-1-naphthyl)-5-(2,6-dihydroxyphenyl)-3-pyrazolyl]carbonylamino}hexanoic acid

HRID 1600078ノート

反応式

HRID 1600078 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[C:16]([C:17]3[C:22]([O:23]C)=[CH:21][CH:20]=[CH:19][C:18]=3[O:25]C)=[CH:15][C:14]([C:27]([NH:29][CH:30]([CH2:34][CH2:35][CH2:36][CH3:37])[C:31]([OH:33])=[O:32])=[O:28])=[N:13]2)=[CH:4][CH:3]=1.B(Br)(Br)Br.O.[OH-].[Na+]>ClCCl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[C:16]([C:17]3[C:18]([OH:25])=[CH:19][CH:20]=[CH:21][C:22]=3[OH:23])=[CH:15][C:14]([C:27]([NH:29][C@@H:30]([CH2:34][CH2:35][CH2:36][CH3:37])[C:31]([OH:33])=[O:32])=[O:28])=[N:13]2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 189266512-{[1-(4-Chloro-1-naphthyl)-5-(2,6-dimethoxyphenyl)-3-pyrazolyl]carbonylamino}hexanoic acid

生成物 1

HCID 136008340(S)-2-{[1-(4-Chloro-1-naphthyl)-5-(2,6-dihydroxyphenyl)-3-pyrazolyl]carbonylamino}hexanoic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-70 °C

実験手順

0.3 g of 2-{[1-(4-chloro-1-naphthyl)-5-(2,6-dimethoxyphenyl)-3-pyrazolyl]carbonylamino}hexanoic acid is dissolved in 6.7 ml of dichloromethane and the mixtureis cooled to -70° C. 5.7 ml of boron tribromide, dissolved in 20 ml of dichlormethane, are added dropwise and the reaction mixture is left for2 hours at -70° C. It is allowed to return to room temperature, and 12 ml of water are then added while cooling. Concentrated NaOH is added topH 14. The aqueous phase is washed with ether and brought to pH 2, the product is extracted with ethyl acetate and the organic phase is dried over sodium sulphate, filtered and evaporated. The residue is crystallisedfrom diisopropyl ether.

後処理

  1. additionare added dropwise
  2. waitthe reaction mixture is left for2 hours at -70° C
  3. customto return to room temperature
  4. temperaturewhile cooling
  5. washThe aqueous phase is washed with ether
  6. extractionthe product is extracted with ethyl acetate
  7. dry with materialthe organic phase is dried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-d006f152a46047e8832b82473e81e309
出典データセット
uspto-grants-1998_04
特許番号
US05744491

反応ノート

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