Water → HCID 178488110, compound
Reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][NH:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=2[NH2:21])[CH2:7][CH2:6]1)=[O:4].O.C1C[O:26][CH2:25]C1>>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([CH2:11][N:12]2[C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=3[NH:21][C:25]2=[O:26])[CH2:9][CH2:10]1)=[O:4]Participants
Procedure
trans-4-[(2-Amino-5-methoxy-phenylamino)-methyl]-cyclohexane carboxylic acid methyl ester (5.4 g, 18.5 mmol) was dissolved in 40 ml of anhydrous THF. 1,1-carbonyldiimidazole (8.9 g, 55.5 mmol) was added and the mixture was stirred for 22 hours. Few drops of water were added and the solvent was removed under reduced pressure and the crude was dissolved in DCM (100 ml) and washed with H2O, a citric acid solution (2×70 ml) and H2O. The organic phase was separated, dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude material was filtered through a silica pad using EtAc/cyclohexane and then EtAc as eluent. The solvent was evaporated and the crude was purified by silica column using EtAc/hexane as eluent. In total 3.2 g of the titled compound were obtained (yield=54%)
Workup
- customthe solvent was removed under reduced pressure
- dissolutionthe crude was dissolved in DCM (100 ml)
- washwashed with H2O
- customThe organic phase was separated
- dry with materialdried over Na2SO4
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- filtrationThe crude material was filtered through a silica pad
- customThe solvent was evaporated
- customthe crude was purified by silica column
Sources & evidence
- ORD record
- ord-716671e5c76f471b94b4a775a970e941
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865704B2
Reaction notes
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