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 1094359Notes

Reaction equation

HRID 1094359 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-8bbfcc9a062e4fcb87597ac326e872d1
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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