Diethyl Ether → HCID 9888076, compound

HRID 987289Notes

Reaction equation

HRID 987289 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].C(N(CC)CC)C.[CH2:12]([O:14][C:15](=[O:37])[CH:16]([O:34][CH2:35][CH3:36])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[CH:20][CH:19]=1)[CH3:13].C(OCC)C>ClCCl>[CH2:12]([O:14][C:15](=[O:37])[CH:16]([O:34][CH2:35][CH3:36])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][C:3](=[O:4])[NH:2][CH3:1])=[CH:31][CH:32]=2)=[CH:20][CH:19]=1)[CH3:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 12228Methyl Isocyanate2×HCID 54239207HCID 54239207, compound

Product 1

HCID 9888076HCID 9888076, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl isocyanate (70 mg; 1.22 mmole) was slowly added to a mixture of triethyl amine (180 mg; 1.17 mmole) and 2-ethoxy-3-{4-[2-(4-hydroxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester (described in Example 26b) (418 mg; 1.17 mmole) in dichloromethane (5 ml). After stirring at room temperature for 2.5 hours the excess of methyl isocyanate was evaporated in vacuo and water and dichloromethane were added. The phases were separated. Water and potassium hydrogensulfate (1 M) were added to the organic phase. The phases were separated, the organic phase was evaporated in vacuo and the residue was purified by chromatography on silica using toluene:diethylether (gradient 4:1 to 3:1) as eluant to give 229 mg (yield 47%) of 2-ethoxy-3-{4-[2-(4-methylcarbamoyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester.

Workup

  1. customwas evaporated in vacuo and water and dichloromethane
  2. additionwere added
  3. customThe phases were separated
  4. additionWater and potassium hydrogensulfate (1 M) were added to the organic phase
  5. customThe phases were separated
  6. customthe organic phase was evaporated in vacuo
  7. customthe residue was purified by chromatography on silica

Sources & evidence

ORD record
ord-d3b1fbb52c7042f6b7ee638686123a22
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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