Water → HCID 19966026, compound

HRID 1734860Notes

Reaction equation

HRID 1734860 reaction equation
C[O-].[Na+].[CH2:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([O:15]C(=O)CC2C3C=CC=CC=3OC3C2=CC=CC=3)[CH2:13][CH3:14])[C:7]=1[NH:33][C:34](=[O:50])[CH2:35][CH:36]1[C:49]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[O:43][C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH3:5].O>C(OCC)C>[CH2:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([OH:15])[CH2:13][CH3:14])[C:7]=1[NH:33][C:34](=[O:50])[CH2:35][CH:36]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:42]=2[O:43][C:44]2[C:49]1=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 19966209HCID 19966209, compound

Product 1

HCID 19966026HCID 19966026, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

9.6 mg (0.18 mmol) of sodium methoxide were added to 3 ml of a methanolic solution containing 37 mg (0.060 mmol) of N-(2-ethyl-6-{1-[2-(9H-xanthen-9-yl)acetoxy]propyl}phenyl)-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 55). The mixture was then stirred for 4 hours at 60° C. At the end of this time, the reaction solution was diluted with diethyl ether. Water was then added to the reaction mixture, and the title compound was distributed between the organic solvent and the water. The organic layer was then separated and washed with water 3 times. The solvent was removed by distillation under reduced pressure, and the resulting residue was subjected to column chromatography through 5 g of silica gel. Elution with mixtures of methylene chloride and ethyl acetate ranging from 10:1 to 5:1 by volume afforded 21 mg (yield 89%) of the title compound as crystals, melting at 167°-168° C. (after recrystallization from a mixture of diethyl ether and hexane).

Sources & evidence

ORD record
ord-b8368639679f4d4fa64caabc922fa505
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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