Lithium hydroxide, monohydrate → [4-(2-Thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine

HRID 1532853ノート

反応式

HRID 1532853 の反応式
C1COCC1.CO.C[O:9][C:10](=[O:40])[C@H:11]([CH2:36][CH2:37][S:38][CH3:39])[NH:12][C:13](=[O:35])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[CH:16][C:15]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34].O.[OH-].[Li+]>O>[S:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[CH2:22][O:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][C@H:11]([C:10]([OH:40])=[O:9])[CH2:36][CH2:37][S:38][CH3:39])=[O:35])=[C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH:16]=1

参加物

5

反応物 3

HCID 168937Lithium hydroxide, monohydrateHCID 21899815MeOH tetrahydrofuranHCID 70224587[4-(2-Thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine methyl ester

生成物 1

HCID 59949455[4-(2-Thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution in 1:1 THF-methanol of [4-(2-thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine methyl ester, prepared as in Example 272C was added a solution of lithium hydroxide hydrate (40 mg, 0.95 mmol) in water (0.5 mL) and the reaction mixture was stirred for 3.5 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between ether and water. Aqueous 2N HCl (1 mL) was added to the aqueous phase. The aqueous phase was extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give [4-(2-thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine. The acid was dissolved in acetonitrile (5 mL) and a solution of lithium hydroxide hydrate (18 mg, 0.43 mmol) in water (8 mL) was added. The mixture was concentrated and the residue was dissolved in water, frozen and lyophilized to give [4-(2-thienylmethoxymethyl)-2-(2-methylphenyl)benzoyl]methionine lithium salt (204 mg) as a light-yellow solid.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between ether and water
  3. additionAqueous 2N HCl (1 mL) was added to the aqueous phase
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7f07216f70d74e39864796ee5bdddeb0
出典データセット
uspto-grants-2001_03
特許番号
US06204293B1

反応ノート

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