Triethylamine → (S,E)-Benzyl 8-(tert-butyldiphenylsilyloxy)-2-methyloct-5-en-4-ylcarbamate

HRID 2065812

반응식

HRID 2065812 반응식
Cl.[Si:2]([O:19][CH2:20][CH2:21]/[CH:22]=[CH:23]/[C@@H:24]([NH2:29])[CH2:25][CH:26]([CH3:28])[CH3:27])([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(CC)CC.Cl[C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39]>C1COCC1.C(Cl)Cl.O>[Si:2]([O:19][CH2:20][CH2:21]/[CH:22]=[CH:23]/[C@@H:24]([NH:29][C:38](=[O:39])[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:25][CH:26]([CH3:27])[CH3:28])([C:15]([CH3:17])([CH3:18])[CH3:16])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 53248329(S,E)-8-(tert-Butyldiphenylsilyloxy)-2-methyloct-5-en-4-amine hydrochloride

생성물 1

HCID 86638859(S,E)-Benzyl 8-(tert-butyldiphenylsilyloxy)-2-methyloct-5-en-4-ylcarbamate수율 72.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mixture of the amine 7 (1.50 g, 3.79 mmol) in dry THF (15 mL) were added Et3N (1.65 mL, 11.75 mmol), and then a solution of benzyl chloroformate (CbzCl, 0.59 mL, 4.17 mmol) in dry THF (4 mL) at 0° C. The resulting white suspension was allowed to warm to rt and stirred for 5 h, then diluted with DCM and water. The aqueous phase was extracted with DCM (2×), and the combined organic layers were washed with 10% HCl and sat. NaHCO3, dried (MgSO4), filtered and concentrated in vacuo. Flash chromatography (SiO2, 8:2, hexanes/EtOAc) afforded 1.45 g (72%) of the title compound as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.75-7.65 (m, 4 H), 7.50-7.28 (m, 11 H), 5.70-5.55 (m, 1H), 5.40 (dd, 1 H, J=15.4, 6.2 Hz), 5.11 (s, 2 H), 4.58 (m, 1 H), 4.21 (m, 1 H), 3.71 (t, 2 H, J=6.6 Hz), 2.30 (q, 2 H, J=6.6 Hz), 1.67 (m, 1 H), 1.40-1.22 (m, 2 H), 1.07 (s, 9 H), 0.92 (m, 6 H); HRMS (ESI) m/z calcd for C33H43NO3SiNa 552.2910, found 552.2930.

후처리

  1. customat 0° C
  2. extractionThe aqueous phase was extracted with DCM (2×)
  3. washthe combined organic layers were washed with 10% HCl and sat. NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0bf44ac47bf04f76b2d2de04d126a678
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288551B2

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