Diisopropylcarbodiimide → HCID 178453874, 화합물

HRID 1497028

반응식

HRID 1497028 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[Cl:29])/[C:22](=[N:24]/O)/[NH2:23].CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C.N1C=CC=CC=1.CCOC(C)=O>[Cl:18][C:19]1[CH:20]=[C:21]([C:22]2[N:24]=[C:15]([C@@H:12]3[CH2:11][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:14][CH2:13]3)[O:17][N:23]=2)[CH:26]=[CH:27][C:28]=1[Cl:29]

참가 물질

8

반응물 3

HCID 12734DiisopropylcarbodiimideHCID 112641853,4-Dichloro-N'-hydroxybenzene-1-carboximidamideHCID 178453971HCID 178453971, 화합물

생성물 1

HCID 178453874HCID 178453874, 화합물수율 57.9%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A microwave vial was charged with cis-4-(tert-butoxycarbonylamino)cyclohexanecarboxylic acid (0.24 g, 0.98 mmol), DMAP (0.12 g, 0.98 mmol) and Intermediate 33A (0.20 g, 0.98 mmol). The reactants were dissolved in DMF (1 mL) and DIC (0.15 mL, 0.98 mmol) was added. The reaction mixture was stirred at rt for 14 h. The reaction mixture was diluted in 3 mL of pyridine. The vial was capped and the reaction mixture was heated in the microwave at 145° C. for 20 minutes, allowed to cool to rt, diluted with EtOAc and washed with water and brine. The solution were concentrated under reduced pressure and purified by flash chromatography with EtOAc/hexanes to give Intermediate 33B (233 mg, 0.565 mmol, 57.9% yield) as a white solid. LCMS=434.1 [M+1], RT=2.43 min (Method B); 1H NMR (500 MHz, chloroform-d) δ ppm 8.19 (1H, d, J=1.93 Hz), 7.92 (1H, dd, J=8.53, 1.93 Hz), 7.56 (1H, d, J=8.25 Hz), 4.59 (1H, br. s.), 3.71 (1H, d, J=9.63 Hz), 3.14-3.22 (1H, m), 2.07-2.17 (2H, m), 1.92-2.02 (2H, m), 1.84 (2H, td, J=8.67, 4.13 Hz), 1.62-1.73 (2H, m), 1.44 (9H, s).

후처리

  1. customThe vial was capped
  2. temperaturethe reaction mixture was heated in the microwave at 145° C. for 20 minutes
  3. temperatureto cool to rt
  4. washwashed with water and brine
  5. concentrationThe solution were concentrated under reduced pressure
  6. custompurified by flash chromatography with EtOAc/hexanes

출처 및 근거

ORD 기록
ord-1e1a5803fc7a49bb97c0f57f7e6e582b
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199946B2

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