Acetic Anhydride → (S)-2-(3-Acetylamino-2-oxo-2H-pyridin-1-yl)-butyric acid tert-butyl ester

HRID 2422687노트

반응식

HRID 2422687 반응식
[C:1]([O:5][C:6](=[O:18])[C@@H:7]([N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:11]1=[O:17])[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>ClCCl>[C:1]([O:5][C:6](=[O:18])[C@@H:7]([N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:26](=[O:28])[CH3:27])[C:11]1=[O:17])[CH2:8][CH3:9])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 60129041(S)-2-(3-Amino-2-oxo-2H-pyridin-1-yl)-butyric acid tert-butyl ester

생성물 1

HCID 57648849(S)-2-(3-Acetylamino-2-oxo-2H-pyridin-1-yl)-butyric acid tert-butyl ester수율 97.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a cooled (0° C.) solution of (S)-2-(3-Amino-2-oxo-2H-pyridin-1-yl)-butyric acid tert-butyl ester (500 mg, 1.98 mmol) in dichloromethane (5 mL) was added triethylamine (220 mg, 2.18 mmol) followed by acetic anhydride (202 mg, 1.98 mmol). The reaction mixture was stirred at room temperature for 12 hours and then partitioned between EtOAc and aqueous 1M HCl. The organic layer was washed with saturated aqueous NaHCO3, brine (30 mL), dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (40% ethyl acetate/hexane) to afford the title compound as a colourless oil (569 mg, 97%): 1H NMR (400 MHz, CDCl3) δ 0.87 (3H, t), 1.40 (9H, s), 1.91 (1H, m), 2.13 (3H, s), 2.19 (1H, m), 5.38 (1H, dd), 6.26 (1H, t), 6.99 (1H, d), 8.33 (1H, d), 8.43 (1H, br s).

후처리

  1. custompartitioned between EtOAc and aqueous 1M HCl
  2. washThe organic layer was washed with saturated aqueous NaHCO3, brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (40% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-3bd157eabb5a4d789a742c95d7b6cb10
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960415B2

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