Potassium Carbonate → [4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]methyl-propanedioic acid, dimethyl ester

HRID 48024

反応式

HRID 48024 の反応式
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].[N:29]1[CH:34]=[CH:33][C:32]([C:35]([OH:48])([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:31][CH:30]=1>O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[OH:48][C:35]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH:32]1[CH2:33][CH2:34][N:29]([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:30][CH2:31]1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 74177alpha,alpha-Diphenyl-4-pyridinemethanolHCID 86585530[4-(4-Chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, dimethyl ester

生成物 1

HCID 86585531[4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]methyl-propanedioic acid, dimethyl ester収率 76%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Mix together [4-(4-chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, dimethyl ester (300 mg, 0.92 mmol), potassium carbonate (350 mg, 2.5 mmol), α-(4-pyridyl)benzhydrol (500 mg, 1.9 mmol), water (3 mL) and toluene (7 mL). Heat the mixture to reflux. After 5 days, cool to room temperature. Add ethyl acetate and water. Wash the organic phase with brine, dry over anhydrous magnesium sulfate and concentrate. Purify by flash chromatography (150 g of silica gel, 10% methanol/chloroform as eluent) to give the title compound (387 mg, 76%). Additionally, compounds derived from all permutations of substituents as set forth in the illustrative examples following Step F can be prepared by the synthetic procedure depicted in Step H.

後処理

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. washWash the organic phase with brine
  4. dry with materialdry over anhydrous magnesium sulfate
  5. concentrationconcentrate
  6. customPurify by flash chromatography (150 g of silica gel, 10% methanol/chloroform as eluent)

出典と根拠

ORDレコード
ord-e67c60553e744b948d31f3eda76ee3ea
出典データセット
uspto-grants-2004_03
特許番号
US06700012B2

関連ノート

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