1,2-Dichloroethane → HCID 68747186, 화합물

HRID 333309노트

반응식

HRID 333309 반응식
[NH2:1][CH2:2][CH:3]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH2:20]([O:27][C:28](=[O:38])[CH2:29][C:30]1([C:35](O)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[NH4+].[OH-]>CN(C=O)C.O.CCOC(C)=O>[CH2:20]([O:27][C:28](=[O:38])[CH2:29][C:30]1([C:35]([NH:1][CH2:2][CH:3]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[C:4]([O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:5])=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

9

반응물 5

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 181649HOAtHCID 596082261-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acidHCID 68749931HCID 68749931, 화합물

생성물 1

HCID 68747186HCID 68747186, 화합물수율 58.8%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of tert-butyl 3-amino-2-(4-methoxybenzyl)propanoate (50 mg, 0.188 mmol), 1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acid (49.4 mg, 0.188 mmol), EDC (47.0 mg, 0.245 mmol) and HOAt (33.3 mg, 0.245 mmol) in DMF (2 ml) was allowed to stir at room temperature for 3 hours. The reaction mixture was diluted with H2O and EtOAc. To the organic layer was added NH4OH (6 ml) and washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 50:50) to give tert-butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-2-(4-methoxybenzyl)propanoate (56.3 mg); Retention time=1.61 minutes (condition B); MS (m+1)=510.5; 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (s, 9H) 1.57-1.70 (m, 6H) 2.00-2.04 (m, 2H) 2.66-2.86 (m, 5H) 3.24-3.47 (m, 2H) 3.77 (s, 3H) 5.08 (s, 2H) 6.36-6.39 (m, 1H) 6.79-6.82 (m, 2H) 7.07-7.11 (m, 2H) 7.30-7.34 (m, 5H).

후처리

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 50:50)

출처 및 근거

ORD 기록
ord-828d46e017ac40c892cfa10968caa45e
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877815B2

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