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

HRID 44146노트

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HRID 44146 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-8538f27e322f45068c5ac77bf9d37850
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541363B2

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