Ethylamine → HCID 67148690, compound

HRID 2428128Notes

Reaction equation

HRID 2428128 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21](O)=[O:22])[CH:16]=[CH:17][C:18]=1[Cl:19])[CH:9]1[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([NH2:26])[CH3:25]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21](=[O:22])[NH:26][CH2:24][CH3:25])[CH:16]=[CH:17][C:18]=1[Cl:19])[CH:9]1[CH2:11][CH2:10]1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 67148302HCID 67148302, compound

Product 1

HCID 67148690HCID 67148690, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a sol. of {3-[(tert-butoxycarbonyl-cyclopropyl-amino)-methyl]-4-chloro-phenyl}-acetic acid (4.30 g, 12.6 mmol) in CH2Cl2 (130 mL) was added 1-chloro-N,N-2-trimethylpropenyl amine (1.87 mL, 15.2 mmol), and the mixture was stirred for 60 min. Ethylamine (2M in THF, 25.0 mL, 50.0 mmol) was added, and the mixture was stirred overnight. More CH2Cl2 was added, and the mixture was washed with water and brine, was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 7:3) yielded the title compound (2.94 g, 63%). LC-MS: tR=0.97 min; ES+: 311.28.

Workup

  1. stirringthe mixture was stirred overnight
  2. washthe mixture was washed with water and brine
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the crude by FC (EtOAc/heptane 7:3)

Sources & evidence

ORD record
ord-3f3a9d7ee5554b738b5e659b63e455f8
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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