Sodium Hydroxide → (S)-2-((S)-2-tert-Butoxycarbonylamino-3,3-dimethyl-butyrylamino)-propionic acid

HRID 44146ノート

反応式

HRID 44146 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:17].[Na+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([NH:8][C@@H:9]([CH3:13])[C:10]([OH:12])=[O:17])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid

生成物 1

HCID 86674881(S)-2-((S)-2-tert-Butoxycarbonylamino-3,3-dimethyl-butyrylamino)-propionic acid収率 191.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (S)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid (18) (6.5 g, 19.7 mmol) in THF (30 mL) was added NaOH (1.7 g, 43.8 mmol) in H2O (60 mL) and the reaction mixture stirred at ambient temperature for 16 h. THF was subsequently removed in vacuo and the aqueous phase washed with EtOAc (50 mL). The aqueous phase was then adjusted to pH ˜2 by addition of 1M HCl and extracted with EtOAc (3×50 mL). The organics were combined dried over MgSO4 and evaporated to give the desired compound (20) as a white solid (5.7 g, 95%); AnalpH2_MeOH; Rt 2.61 min; m/z 303 (MH+); white solid

後処理

  1. customTHF was subsequently removed in vacuo
  2. washthe aqueous phase washed with EtOAc (50 mL)
  3. additionThe aqueous phase was then adjusted to pH ˜2 by addition of 1M HCl
  4. extractionextracted with EtOAc (3×50 mL)
  5. dry with materialThe organics were combined dried over MgSO4
  6. customevaporated

出典と根拠

ORDレコード
ord-8538f27e322f45068c5ac77bf9d37850
出典データセット
uspto-grants-2013_09
特許番号
US08541363B2

反応ノート

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