Water → 1-Cyclohexyloxycarbonyloxyethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate

HRID 2370916Notes

Reaction equation

HRID 2370916 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][CH:10]([C:14]2[N:15]=[CH:16][N:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:18]=2)[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[CH:25]1([O:31][C:32]([O:34][CH:35](Cl)[CH3:36])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[NH2:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][CH:10]([C:14]2[N:15]=[CH:16][N:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:18]=2)[C:11]([O:13][CH:35]([O:34][C:32]([O:31][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:33])[CH3:36])=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 112295291-Chloroethyl Cyclohexyl CarbonateHCID 694540453-(6-Aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionic acid hydrochloride

Product 1

HCID 116487441-Cyclohexyloxycarbonyloxyethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionateYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 50.0 mg (0.16 mmol) of the compound from example 1i and 39 mg (0.19 mmol) of 1-cyclohexyloxycarbonyloxy-1-ethyl chloride, 13 mg (0.08 mmol) of KI and 26 mg (0.19 mmol) of K2CO3 in 2 ml of DMF was stirred at 60° C. for 12 h. Then 5 ml of water were added and the reaction solution was extracted several times with EA. The combined EA extracts were dried, filtered and concentrated to dryness. The resulting residue was purified on silica gel with CH2Cl2/methanol as mobile phase, resulting in 32 mg of the title compound in the form of an amorphous solid.

Workup

  1. extractionthe reaction solution was extracted several times with EA
  2. dry with materialThe combined EA extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe resulting residue was purified on silica gel with CH2Cl2/methanol as mobile phase

Sources & evidence

ORD record
ord-cc0d635853b74da9a230ff0d40108b32
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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