tert-Butanol → HCID 53722169, 화합물

HRID 1055260노트

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HRID 1055260 반응식
C1CCC(N=C=NC2CCCCC2)CC1.[CH3:16][C:17]([OH:20])([CH3:19])[CH3:18].[NH:21]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:22]([C:35](O)=[O:36])[CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[NH:21]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:22]([C:35]([O:20][C:17]([CH3:19])([CH3:18])[CH3:16])=[O:36])[CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26]

참가 물질

6

반응물 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 2755950Boc-dap(Z)-OH

생성물 1

HCID 53722169HCID 53722169, 화합물수율 84%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
20 °C

실험 절차

To an ice-cold CH2Cl2 (60 mL) solution of DCC (9.78 g, 47.34 mmol), t-BuOH (17.54 g, 0.24 mol) and DMAP (0.29 g, 2.37 mmol); a CH2Cl2 (40 mL) solution of 2 (16.00 g, 47.34 mmol) was added slowly over 20 min. Then reaction mixture was allowed to stir 1 h at 0° C. and 10 h at 20° C. Precipitated urea was then filtered off and the filtrate evaporated in vacuo. The residue was taken up in CH2Cl2, and if necessary, filtered free of any further precipitated urea. The CH2Cl2 solution was washed twice with 10% citric acid solution and with saturated NaHCO3 solution, and then dried over Na2SO4. The residue obtained after evaporation of CH2Cl2 was purified by column chromatography to obtain the product as a clear viscous oil (15.67 g, 84% yield). 1H NMR (300 MHz, CDCl3) δ7.26 (5H), 5.53 (1H), 5.45 (1H), 5.02 (2H), 4.26-4.18 (1H), 3.59-3.46 (2H), 1.38 (9H), 1.37 (9H); 13C NMR (75 MHz, CDCl3) δ 169.9, 156.8, 155.8, 136.6, 128.7, 128.3, 82.8, 80.1, 66.9, 54.7, 43.3, 28.5, 28.1; ESI-LRMS m/z 395.2 (M+H)+, 417.2 (M+Na)+.

후처리

  1. customThen reaction mixture
  2. filtrationPrecipitated urea was then filtered off
  3. customthe filtrate evaporated in vacuo
  4. filtrationif necessary, filtered free of
  5. customany further precipitated urea
  6. washThe CH2Cl2 solution was washed twice with 10% citric acid solution and with saturated NaHCO3 solution
  7. dry with materialdried over Na2SO4
  8. customThe residue obtained
  9. customafter evaporation of CH2Cl2
  10. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-5ccdf864f5884dd08d195f5bb829f84e
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394338B2

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