1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → ((S)-{(3,4-dimethyl-phenyl)-[2-(5-methyl-pyridin-2-yl)-ethyl]-carbamoyl}-phenyl-methyl)-carbamic acid tert-butyl ester

HRID 1094359ノート

反応式

HRID 1094359 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:19][C:20]([O:23][C:24]([NH:26][C@H:27]([C:34](O)=[O:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])([CH3:22])[CH3:21].Cl.CN(C)CCCN=C=NCC>ClCCl>[C:20]([O:23][C:24](=[O:25])[NH:26][C@H:27]([C:34](=[O:35])[N:9]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:22])([CH3:19])[CH3:21]

参加物

5

反応物 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11010409(2S)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acidHCID 58007613(3,4-Dimethyl-phenyl)-[2-(5-methyl-pyridin-2-yl)-ethyl]-amine

生成物 1

HCID 58007500((S)-{(3,4-dimethyl-phenyl)-[2-(5-methyl-pyridin-2-yl)-ethyl]-carbamoyl}-phenyl-methyl)-carbamic acid tert-butyl ester収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of 35 mg (0.15 mmol) (3,4-dimethyl-phenyl)-[2-(5-methyl-pyridin-2-yl)-ethyl]-amine and 40.4 mg (0.16 mmol) Boc-L-alpha-phenylglycine in 540 uL dichloromethane under argon, was added 31.4 mg (0.16 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The mixture was stirred at 0° C. for 3 hours then at ambient temperature overnight. The solution was washed once with a sat. NaHCO3 solution (3 mL) and once with water (3 mL). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.052 g (75%) of the title compound as an oil. MS (m/e): 474.3 [M+H]+.

後処理

  1. customat ambient temperature
  2. customovernight
  3. washThe solution was washed once with a sat. NaHCO3 solution (3 mL) and once with water (3 mL)
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
  8. customformed from heptane and ethylacetate

出典と根拠

ORDレコード
ord-8bbfcc9a062e4fcb87597ac326e872d1
出典データセット
uspto-grants-2012_03
特許番号
US08133909B2

反応ノート

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