Hydrochloric Acid → 3-(Cyanomethyl)-5-[(dipropylamino)carbonyl]benzoic acid

HRID 1350976

反応式

HRID 1350976 の反応式
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([C:15]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[O:16])[CH:14]=1)[C:7]([O:9]CC)=[O:8])#[N:2].O.[OH-].[Li+].Cl>C(O)C.O>[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([C:15]([N:17]([CH2:18][CH2:19][CH3:20])[CH2:21][CH2:22][CH3:23])=[O:16])[CH:14]=1)[C:7]([OH:9])=[O:8])#[N:2]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21086102Ethyl 3-(cyanomethyl)-5-[(dipropylamino)carbonyl)benzoate

生成物 1

HCID 210857723-(Cyanomethyl)-5-[(dipropylamino)carbonyl]benzoic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

A mixture of ethyl 3-[(dipropylamino)carbonyl]-5-(hydroxymethyl)benzoate (1.5 g) and phosphorous tribromide (0.95 mL) is stirred in dichloromethane (10 mL) and heated at 50 degrees C. for 4 hours and then cooled and partitioned between dichloromethane and water. The organic phase is separated and washed with aqueous sodium bicarbonate and then dried over magnesium sulfate and taken to dryness to give ethyl 3-(bromomethyl)-5-[(dipropylamino)carbonyl]benzoate, high resolution MS MH+=370.1020. Ethyl 3-(bromomethyl)-5-[(dipropylamino)carbonyl]benzoate (1.4 g) and sodium cyanide (0.2 g) are stirred in dry DMSO (25 mL) at 20–25 degrees C. for 3.5 hours and the mixture is then partitioned between ethyl acetate, water and saline. The organic layer is separated and dried over magnesium sulfate and taken to dryness under reduced pressure to give ethyl 3-(cyanomethyl)-5-[(dipropylamino)carbonyl]benzoate. Ethyl 3-(cyanomethyl)-5-[(dipropylamino)carbonyl]benzoate (0.6 g) is hydrolyzed with lithium hydroxide monohydrate (0.1 g) in ethanol and water at 20–25 degrees C. overnight and then added to water (50 mL). The pH is adjusted to 4 using concentrated hydrochloric acid and the mixture is partitioned between ethyl acetate, water, and saline. The organic phase is separated and dried over magnesium sulfate and taken to dryness under reduced pressure to give 3-(cyanomethyl)-5-[(dipropylamino)carbonyl]benzoic acid, MS M+H=287.2.

後処理

  1. customthe mixture is partitioned between ethyl acetate, water, and saline
  2. customThe organic phase is separated
  3. dry with materialdried over magnesium sulfate

出典と根拠

ORDレコード
ord-169516fd2b1c4a50857b15d2590249db
出典データセット
uspto-grants-2007_05
特許番号
US07214715B2

関連ノート

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