Water → (R)-4-(4-((4'-chlorobiphenyl-2-yl)(dimethoxyphosphoryloxy)methyl)piperidin-1-yl)benzoic acid

HRID 1476332ノート

反応式

HRID 1476332 の反応式
[OH-].[Li+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C@H:16]([O:34][P:35]([O:39][CH3:40])([O:37][CH3:38])=[O:36])[CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29]CC)=[O:28])=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[CH:6][CH:5]=1.C1COCC1.O>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C@H:16]([O:34][P:35]([O:37][CH3:38])([O:39][CH3:40])=[O:36])[CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:33]=[CH:32][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58080150(R)-ethyl 4-(4-((4'-chlorobiphenyl-2-yl)(dimethoxyphosphoryloxy)methyl)piperidin-1-yl)benzoate2 回

生成物 1

HCID 58080233(R)-4-(4-((4'-chlorobiphenyl-2-yl)(dimethoxyphosphoryloxy)methyl)piperidin-1-yl)benzoic acid収率 57%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
35 °C

実験手順

A mixture of lithium hydroxide (107 mg, 4.48 mmol), (R)-ethyl 4-(4-((4′-chlorobiphenyl-2-yl)(dimethoxyphosphoryloxy)methyl)piperidin-1-yl)benzoate (INTERMEDIATE 121, 500 mg, 0.9 mmol), THF (10 ml), water (2.5 ml), and MeOH (2.5 ml) was heated at 35° C. overnight. The reaction mixture was concentrated under reduced pressure, diluted with water (10 ml) and acidified with an aqueous solution of 6 N HCl, resulting in a precipitate. The solid was collected by filtration to give the title compound (270 mg, yield: 57%). The title compound was used in the preparation of EXAMPLE 30 without further purification.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water (10 ml)
  3. customresulting in a precipitate
  4. filtrationThe solid was collected by filtration

出典と根拠

ORDレコード
ord-e194375ee018424d91e1e28d6771441c
出典データセット
uspto-grants-2015_04
特許番号
US09018381B2

反応ノート

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