Methyl Carbamate → HCID 22013854, compound

HRID 1532724Notes

Reaction equation

HRID 1532724 reaction equation
[CH3:1][O:2][C:3]([CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:12][CH:11]=1)[C:6](O)=[O:7])=[O:4].S(Cl)(Cl)=O.[C:35](=[O:39])([O:37][CH3:38])[NH2:36]>C1C=CC=CC=1>[CH3:38][O:37][C:35]([NH:36][C:6]([CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[O:22][C:23]=2[CH3:24])=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:7])=[O:39]

Participants

5

Reactant 3

HCID 11722Methyl CarbamateHCID 24386Thionyl ChlorideHCID 9866203HCID 9866203, compound

Product 1

HCID 22013854HCID 22013854, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
85 °C

Procedure

2-Methoxycarbonyl-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionic acid (2.00 g, 4.89 mmol) obtained in Example 1 was dissolved in benzene (15 ml), and thionyl chloride (392 μl, 5.38 mmol) was added at room temperature. The mixture was refluxed under heating for 1.5 hr and the solvent was evaporated. The residue was dissolved in toluene (6 ml), and methyl carbamate (440 mg, 5.87 mmol) was added. at room temperature. The mixture was stirred at 80-90° C. for 30 min. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (developing solvent; chloroform: methanol=30:1). The obtained white solid was recrystallized from methanol to give the title compound (1.40 g, yield 61%).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 1.5 hr
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in toluene (6 ml)
  5. customat room temperature
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography (developing solvent; chloroform: methanol=30:1)
  8. customThe obtained white solid was recrystallized from methanol

Sources & evidence

ORD record
ord-b5bbd020914c41c8a74a53a3526a9112
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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