Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate

HRID 529548노트

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HRID 529548 반응식
O=[CH:2][CH2:3][C@H:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:5].[C:14]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:16][CH2:17][CH3:18])=[O:15]>C1COCC1>[C:9]([O:8][C:7]([NH:6][C@H:4]([CH3:5])[CH2:3]/[CH:2]=[CH:19]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:13])([CH3:12])([CH3:11])[CH3:10]

참가 물질

4

반응물 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 25231755tert-butyl N-[(2R)-4-oxobutan-2-yl]carbamate

생성물 1

HCID 86706226(R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate수율 80.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (R)-tert-butyl 4-oxobutan-2-ylcarbamate (1.54 g, 8.22 mmol) in THF (25 mL) at rt was added (carbethoxymethylene)triphenylphosphorane (6.30 g, 18.1 mmol) in portions. The resulting clear solution was stirred at rt under argon for 3 days. The reaction mixture was concentrated and the oily residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-60% EtOAc/Hex to give (R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate (1.70 g, 6.61 mmol, 80% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 6.91 (dt, J=15.3, 7.5 Hz, 1H), 5.92-5.82 (m, 1H), 4.37 (s, 1H), 4.19 (q, J=7.1 Hz, 2H), 3.83 (s, 1H), 2.37 (t, J=6.6 Hz, 2H), 1.44 (s, 9H), 1.29 (t, J=7.1 Hz, 3H), 1.15 (d, J=6.7 Hz, 3H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe oily residue was purified
  3. washeluting with a gradient of 0-60% EtOAc/Hex

출처 및 근거

ORD 기록
ord-a199d04452e44054a22ecb80c731ccf8
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346852B2

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