Sodium Methoxide → HCID 178450807、化合物

HRID 2169292ノート

反応式

HRID 2169292 の反応式
[C:1]1([C:7]2([CH2:13][C:14]([NH2:16])=[NH:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O:18][C:19](=O)/[C:20](/[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[C:21](\O)/[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C[O-].[Na+]>CO.ClCCl>[C:25]([O:24][C:22]([C:21]1[C:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:19]([OH:18])[N:16]=[C:14]([CH2:13][C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[N:15]=1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

参加物

6

反応物 3

HCID 10942334Sodium MethoxideHCID 546790054-Tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarateHCID 867259372-(1-Phenyl-cyclohexyl)-acetamidine

生成物 1

HCID 178450807HCID 178450807、化合物収率 85.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a mixture of HCl-salt of 2-(1-phenyl-cyclohexyl)-acetamidine (254) (2.0 g, 7.91 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (9) (3.66 g, 11.86 mmol) in methanol (50.0 mL) was added sodium methoxide (1.28 g, 23.73 mmol, 25% in methanol) at 0° C. Then the reaction mixture was allowed to warm up to room temperature and was stirred for 16 h. After completion of the reaction, the solvent was reduced and the crude product was dissolved in dichloromethane and the resultant mixture extracted with dichloromethane. The organic layer was washed with 1N HCl and with water and brine. It was then dried over Na2SO4 and concentrated. The crude product was purified by normal silica gel column chromatography (using 10% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (255) (3.2 g, 85.0%) as a yellowish thick liquid which turned into a solid after storing at room temperature.

後処理

  1. customAfter completion of the reaction
  2. extractionthe resultant mixture extracted with dichloromethane
  3. washThe organic layer was washed with 1N HCl and with water and brine
  4. dry with materialIt was then dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by normal silica gel column chromatography (using 10% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-b3f02e5602d2400e84462248455039fc
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

読み込み中…