Chloroform → tert-Butyl 2-[3-(N-Cyclohexylaminocarbonylmethyl)phenoxy]-2-methylpropionate

HRID 480688Notes

Reaction equation

HRID 480688 reaction equation
[C:1]([O:5][C:6]([C:8]([CH3:21])([O:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18]([OH:20])=O)[CH:14]=[CH:15][CH:16]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[CH:28]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(Cl)(Cl)Cl>ClCCl>[CH:28]1([NH:34][C:18]([CH2:17][C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=2)[O:10][C:8]([CH3:9])([CH3:21])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:20])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7965CyclohexylamineHCID 65578Oxalyl chlorideHCID 187664143-(1-tert-Butoxycarbonyl-1-methylethoxy)phenylacetic Acid

Product 1

HCID 18766566tert-Butyl 2-[3-(N-Cyclohexylaminocarbonylmethyl)phenoxy]-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(1-tert-Butoxycarbonyl-1-methylethoxy)phenylacetic acid (250 mg, 0.849 mmol) was dissolved in solvent mixture of dimethylformamide (10 μL)-dichloromethane (6 mL). Subsequently, oxalyl chloride [(COCl)2 (148 μL, 1.70 mmol)] was added at 0° C., the mixture was stirred for one hour at room temperature. The reaction mixture was added to a solution obtained by dissolving cyclohexylamine (0.97 mL, 8.49 mmol) in dichloromethane (1 mL) at 0° C., the mixture was stirred for one hour at room temperature. Chloroform was added to the reaction mixture. Washing was performed sequentially with 1M hydrochloric acid, water, and saturated brine, followed by drying over sodium sulfate. The mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (chloroform/methanol=50/1), whereby the target compound was obtained (280 mg, 0.746 mmol, 87.8%).

Workup

  1. additionThe reaction mixture was added to a solution
  2. customobtained
  3. stirringthe mixture was stirred for one hour at room temperature
  4. washWashing
  5. dry with materialby drying over sodium sulfate
  6. concentrationThe mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (chloroform/methanol=50/1), whereby the target compound
  7. customwas obtained (280 mg, 0.746 mmol, 87.8%)

Sources & evidence

ORD record
ord-6e3d8b7d82454c8fab97b872deaf0c65
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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