Sodium Chloride → HCID 54304223, compound

HRID 1017999Notes

Reaction equation

HRID 1017999 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([Li])CCC.[C:12]([O:16][C:17](=[O:49])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:48])[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[CH3:45])=[O:37])=[C:31]([O:46][CH3:47])[CH:30]=2)=[CH:22][CH:21]=1)([CH3:15])([CH3:14])[CH3:13].[H-].[Na+].[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:12]([O:16][C:17](=[O:49])[CH2:18][CH:19]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:48])[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[CH3:45])=[O:37])=[C:31]([O:46][CH3:47])[CH:30]=2)=[CH:22][CH:21]=1)[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)([CH3:13])([CH3:15])[CH3:14]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 8083MorpholineHCID 24758Sodium hydrideHCID 54055857HCID 54055857, compoundHCID 178418339Butyllithium

Product 1

HCID 54304223HCID 54304223, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of morpholine (87 mg) in anhydrous tetrahydrofuran (10 ml), cooled to −78° C. and under an atmosphere of nitrogen, was treated with a solution of n-butyl lithium in hexanes (0.4 ml, 2.5M). After stirring at −78° C. for 15 minutes the mixture was treated dropwise with a solution produced from treating a stirred suspension of 3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}phenyl)-propenoic acid tert-butyl ester (0.25 g, Reference Example 8) in anhydrous tetrahydrofuran (10 ml) with sodium hydride (58 mg of a 60% dispersion in mineral oil), under an atmosphere of nitrogen. The resulting mixture was stirred a further 30 minutes at −78° C. then poured into a mixture of ethyl acetate (50 ml) and saturated aqueous sodium chloride solution (50 ml). The organic layer was separated, then dried over magnesium sulphate and then evaporated. The residue was triturated with diethyl ether to give the title compound (165 mg) as a white solid.

Workup

  1. additionwas treated dropwise with a solution
  2. customproduced
  3. additionfrom treating
  4. stirringThe resulting mixture was stirred a further 30 minutes at −78° C.
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-d7776b66cf954a8bbf450127ae62f675
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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