Hydroxyacetone → HCID 53762937、化合物

HRID 234244

反応式

HRID 234244 の反応式
[CH3:1][O:2][C:3](=[O:36])[C:4]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[CH:7]=[C:6]([O:13][Si](C)(C)C(C)(C)C(C)C)[C:5]=1[CH2:23][S:24][CH2:25][C@H:26]([NH:33][C:34]#[N:35])[C:27]1[O:31][N:30]=[C:29]([CH3:32])[N:28]=1.[OH:37][CH2:38][C:39](=O)[CH3:40]>O1CCCC1.[OH-].[Na+].O>[CH3:1][O:2][C:3](=[O:36])[C:4]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[CH:7]=[C:6]([OH:13])[C:5]=1[CH2:23][S:24][CH2:25][C@@H:26]([C:27]1[O:31][N:30]=[C:29]([CH3:32])[N:28]=1)[NH:33][C:34]1[O:37][CH:38]=[C:39]([CH3:40])[N:35]=1

参加物

6

反応物 2

HCID 8299HydroxyacetoneHCID 53958922HCID 53958922、化合物

生成物 1

HCID 53762937HCID 53762937、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
40 °C

実験手順

To a stirred solution of 260 mg of (R)-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-[2-cyanoamino-2-(3-methyl-1,2,4-oxadiazol-5-yl)-ethylsulfanylmethyl]-5-methoxy-6-methyl-benzoic acid methyl ester in 50 ml of tetrahydrofuran were added 0.1 ml of 25% aqueous hydroxyacetone and 0.09 ml of IN sodium hydroxide solution. The suspension was stirred for 12 h at 40° C. After cooling, the mixture was diluted with 100 ml water and subsequently extracted with 200 ml ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using ethyl acetate/hexane (1:1, v/v) as eluent, and the purified product was treated with ammonium fluoride in methanol in an analogous manner to the procedure described in Example 1 to yield (R)-3-hydroxy-5-methoxy-6-methyl-2-[2-(3-methyl-1,2,4-oxadiazol-5-yl)-2-(4-methyl-oxazol-2-ylamino)-ethylsulfanylmethyl]-benzoic acid methyl ester as a white powder.

後処理

  1. temperatureAfter cooling
  2. extractionsubsequently extracted with 200 ml ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel
  7. additionv/v) as eluent, and the purified product was treated with ammonium fluoride in methanol in an analogous manner to the procedure

出典と根拠

ORDレコード
ord-a633276c06fc4c00988a5def4b3ad5a4
出典データセット
uspto-grants-1997_01
特許番号
US05594135

関連ノート

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