Lithium hydroxide, monohydrate → (S)-2-(tert-Butoxycarbonylamino)-3-(4-(phenylsulfonyl)phenyl)propanoic Acid

HRID 600337ノート

反応式

HRID 600337 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)(=[O:22])=[O:23])=[CH:17][CH:16]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 11316088(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(phenylsulfonyl)phenyl)propanoate

生成物 1

HCID 57999674(S)-2-(tert-Butoxycarbonylamino)-3-(4-(phenylsulfonyl)phenyl)propanoic Acid収率 99.8%

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)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(phenylsulfonyl)phenyl)propanoate (700 mg) in THF (15 mL) and water (10 mL) was added lithium hydroxide monohydrate (140 mg). 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 subtitle compound (675 mg) 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-c800877926b842e2ba0504c68f318c1a
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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