Succinic anhydride → 3-(Bis(((t-butyloxy)carbonyl)methyl)carbamoyl)propanoic acid

HRID 1397110노트

반응식

HRID 1397110 반응식
[C:1]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH2:2][NH:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1.C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl.ClCCl>[C:14]([O:13][C:1]([CH2:2][N:3]([CH2:4][C:5]([O:7][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:6])[C:18]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:24])=[O:12])([CH3:17])([CH3:16])[CH3:15]

참가 물질

6

반응물 3

HCID 7922Succinic anhydrideHCID 81531DiisopropylethylamineHCID 4393691DI-T-Butyl iminodiacetate

생성물 1

HCID 866665243-(Bis(((t-butyloxy)carbonyl)methyl)carbamoyl)propanoic acid수율 72.6%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

Compound 14 (0.88 g, 3.59 mmol), succinic anhydride (0.377 g, 3.77 mmol), ethyldiisopropylamine (625 μL, 3.59 mmol) and 4-di(methylamino)pyridine (44 mg, 0.359 mmol) were dissolved in CHCl3 (15 mL) and stirred for 48 h. The mixture was diluted with dichloromethane (140 mL) and the organic layer was washed with H2O (2×75 mL) and saturated aqueous NaCl, dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (80% EtOAc in hexanes) to give the compound 15 (0.9 g, 72.6%). 1H NMR (400 MHz, CDCl3) δ 1.44 (s, 9H), 1.47 (s, 9H), 2.62 (t, J=5.8, 2H), 2.69 (t, J=5.8, 2H), 4.02 (s, 2H), 4.06 (s, 2H). ESI-MS calculated for C16H27NO7, 345.59 found 368.1 (M+Na).

후처리

  1. washthe organic layer was washed with H2O (2×75 mL) and saturated aqueous NaCl
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by silica gel chromatography (80% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-1418035c9c3440b891b7576b7d241d9d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901072B2

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