Cyclohexyl isocyanate → Ethyl(({1-[(cyclohexylamino)carbonyl]piperidin-4-yl}methyl){4-[(dodecylamino)carbonyl]benzyl}amino)(oxo)acetate

HRID 735851Notes

Reaction equation

HRID 735851 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[C:5]([N:7]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])=[CH:18][CH:17]=1)[CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:6])[CH3:2].[CH:38]1([N:44]=[C:45]=[O:46])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>C1COCC1>[CH2:1]([O:3][C:4](=[O:37])[C:5]([N:7]([CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:45]([NH:44][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[O:46])[CH2:13][CH2:14]1)[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])=[CH:20][CH:21]=1)=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 67186073Ethyl[{4-[(dodecylamino)carbonyl]benzyl}(piperidin-4-ylmethyl)amino](oxo)acetate

Product 1

HCID 67186835Ethyl(({1-[(cyclohexylamino)carbonyl]piperidin-4-yl}methyl){4-[(dodecylamino)carbonyl]benzyl}amino)(oxo)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The resin-bound ethyl[{4-[(dodecylamino)carbonyl]benzyl}(piperidin-4-ylmethyl)amino]-(oxo)acetate (described in step h, 0.0426 mmol) was swelled in THF (0.5 mL) for 15 min at rt. Cyclohexyl isocyanate (18 mg, 0.143 mmol) dissolved in THF (0.9 mL) and TEA (29 mg, 0.282 mmol) was added and the reaction mixture was shaken 14 h at rt. The resin was washed successively with THF (1×0.15 min), MeOH (1×15 min), THF (1×15 min), MeOH (3×10 min), DMF (3×10 min), MeOH (1×5 min), THF (3×10 min), MeOH (1×5 min), DCM (3×10 min) and with Et2O (1×10 min). The resin was then dried under vacuum to afford the title compound which was used directly in the next step.

Workup

  1. washThe resin was washed successively with THF (1×0.15 min), MeOH (1×15 min), THF (1×15 min), MeOH (3×10 min), DMF (3×10 min), MeOH (1×5 min), THF (3×10 min), MeOH (1×5 min), DCM (3×10 min) and with Et2O (1×10 min)
  2. customThe resin was then dried under vacuum

Sources & evidence

ORD record
ord-f4fb0352a5c34b6ea7448793a6da6f7f
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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