Lithium hydroxide, monohydrate → (1R,2R)-2-(4-Bromophenyl)-1-((S)-1-(tert-butoxycarbonyl)piperidine-2-carboxamido)cyclopropanecarboxylic Acid

HRID 600312ノート

反応式

HRID 600312 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@:9]2([NH:15][C:16]([C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:17])[C:11]([O:13]C)=[O:12])=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:10][C@:9]2([NH:15][C:16]([C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:17])[C:11]([OH:13])=[O:12])=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 57999639(S)-tert-butyl 2-((1R,2R)-2-(4-bromophenyl)-1-(methoxycarbonyl)cyclopropylcarbamoyl)piperidine-1-carboxylate

生成物 1

HCID 57999663(1R,2R)-2-(4-Bromophenyl)-1-((S)-1-(tert-butoxycarbonyl)piperidine-2-carboxamido)cyclopropanecarboxylic Acid収率 99.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of (S)-tert-butyl 2-((1R,2R)-2-(4-bromophenyl)-1-(methoxycarbonyl)-cyclopropylcarbamoyl)piperidine-1-carboxylate (3 g) in THF (45 mL) and water (30 mL) was added lithium hydroxide monohydrate (0.298 g). The mixture was stirred at RT for 2 h. The mixture was partitioned between 0.1 N HCl(aq) and ethyl acetate, and the aqueous phase was extracted twice more with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated in vacuo to leave the title compound (2.90 g) as a white solid.

後処理

  1. customThe mixture was partitioned between 0.1 N HCl(aq) and ethyl acetate
  2. extractionthe aqueous phase was extracted twice more with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7bdb20dbd7cd4cf78ea8361174e6a0b4
出典データセット
uspto-grants-2011_03
特許番号
US07902181B2

反応ノート

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