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

HRID 14024

반응식

HRID 14024 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6f7a1015b1c1477c82efd7aeb01603f8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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