Lithium Hydroxide → 2-[(4-{2-[Benzyl(hexyl)amino]-2-oxoethyl}phenoxy)methyl]benzoic acid

HRID 899873

反応式

HRID 899873 の反応式
[CH2:1]([N:8]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:9](=[O:29])[CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21]C)=[O:20])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[CH2:1]([N:8]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:9](=[O:29])[CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([OH:21])=[O:20])=[CH:13][CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 69120595Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate

生成物 1

HCID 100043962-[(4-{2-[Benzyl(hexyl)amino]-2-oxoethyl}phenoxy)methyl]benzoic acid収率 35.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate (70 mg, 0.148 mmol) in THF (2 ml) was cooled in an ice-bath. Lithium hydroxide (7.08 mg, 0.296 mmol) in water (1 ml) was dropped in. The cooling-bath was then removed and the mixture was stirred overnight. HPLC showed that the reaction was not complete. More lithium hydroxide (0.2M, 0.5 ml) was added. The reaction mixture was stirred for 4 days more. It was then evaporated in vacuum to remove THF. The residue was acidified with 1% hydrochloric acid, pH=3-4, and extracted with ethyl acetate. The organic phase was dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM, MeOH/DCM (1:99, and then 2:98) as eluant gave 24 mg the desired product, yield 35%.

後処理

  1. customThe cooling-bath was then removed
  2. additionMore lithium hydroxide (0.2M, 0.5 ml) was added
  3. stirringThe reaction mixture was stirred for 4 days more
  4. customIt was then evaporated in vacuum
  5. customto remove THF
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic phase was dried (magnesium sulphate)
  8. customevaporated

出典と根拠

ORDレコード
ord-6a2ceaa30bf049d6a46657bf3b6b6bba
出典データセット
uspto-grants-2008_04
特許番号
US07355069B2

関連ノート

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