1,2-Dichloroethane → HCID 68747186、化合物

HRID 333309ノート

反応式

HRID 333309 の反応式
[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

参加物

9

反応物 5

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

生成物 1

HCID 68747186HCID 68747186、化合物収率 58.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-828d46e017ac40c892cfa10968caa45e
出典データセット
uspto-grants-2014_11
特許番号
US08877815B2

反応ノート

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