Triethylamine → trans-[2-(Acryloyl-but-3-enyl-amino)-cyclohexyl]-carbamic acid tert-butyl ester

HRID 2218563Notes

Reaction equation

HRID 2218563 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]([O:10][C:11](=[O:24])[NH:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[NH:19][CH2:20][CH2:21][CH:22]=[CH2:23])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl>[C:6]([O:10][C:11](=[O:24])[NH:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[N:19]([C:1](=[O:4])[CH:2]=[CH2:3])[CH2:20][CH2:21][CH:22]=[CH2:23])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 68975768trans-(2-But-3-enylamino-cyclohexyl)-carbamic acid tert-butyl ester

Product 1

HCID 68977079trans-[2-(Acryloyl-but-3-enyl-amino)-cyclohexyl]-carbamic acid tert-butyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acryloyl chloride (47 mg, 0.50 mmol) was added at 0° C. to a solution of trans-(2-but-3-enylamino-cyclohexyl)-carbamic acid tert-butyl ester (123 mg, 0.46 mmol) and triethylamine (51 mg, 0.51 mmol) in dichloromethane (3 ml), and the reaction mixture was allowed to reach room temperature over 3 h. After partitioning between dichloro-methane and 10% aq. citric acid solution, the organic layer was washed with 1 M aq. sodium carbonate solution and brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (103 mg, 70%). Light yellow solid, MS (ISP) 323.3 (M+H)+.

Workup

  1. customAfter partitioning between dichloro-methane and 10% aq. citric acid solution
  2. washthe organic layer was washed with 1 M aq. sodium carbonate solution and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-e05a5fd72dba48aaa26e275304f45c3d
Source dataset
uspto-grants-2008_08
Patent number
US07411093B2

Reaction notes

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