Phthalic Anhydride → (2S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid tert-butyl ester

HRID 2110812노트

반응식

HRID 2110812 반응식
Cl.[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.[C:21]1(=O)[O:26][C:24](=[O:25])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12>C1(C)C=CC=CC=1.CCOCC>[C:2]([O:6][C:7](=[O:11])[C@@H:8]([N:9]1[C:24](=[O:25])[C:23]2[C:22](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]1=[O:26])[CH3:10])([CH3:5])([CH3:4])[CH3:3]

참가 물질

6

반응물 3

HCID 6811Phthalic AnhydrideHCID 81531DiisopropylethylamineHCID 11275390tert-Butyl alaninate hydrochloride

생성물 1

HCID 13005797(2S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid tert-butyl ester수율 90%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

A suspension of (2S) alanine tert-butyl ester hydrochloride (2.05 g, 11.2 mmol), diisopropylethylamine (1.83 mL, 10.6 mmol) and phthalic anhydride (1.48 g, 10 mmol) in toluene (10 mL) was refluxed for 3 hours under Dean-Stark conditions. The reaction was cooled to room temperature, diluted with Et2O, washed with 1N HCl and then with aq.sat. NaHCO3. The organic layer was dried (MgSO4), filtered and evaporated to afford the sub-title compound as a white powder (2.465 g, 90%): 1H NMR (400 MHz CDCl3) δ 1.45 (9H, s), 1.68 (3H, d), 4.90 (1H, q), 7.75 (2H, d), 7.88 (2H, d)

후처리

  1. temperaturewas refluxed for 3 hours under Dean-Stark conditions
  2. washwashed with 1N HCl
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-fbf1b0d61f6244fc8ca95ce1bc39d8c7
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517987B2

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