5-[3-(Ethoxycarbonyl)benzoyl]-2-hydroxybenzenepropanoic acid ethyl ester → HCID 19922077, compound

HRID 1647984Notes

Reaction equation

HRID 1647984 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:18]=[CH:17][C:11]2[C:12](=[O:16])[CH2:13][CH2:14][O:15][C:10]=2[C:9]=1[CH2:19][CH2:20][CH3:21].C([O:24][C:25](=[O:48])[CH2:26][CH2:27][C:28]1[CH:33]=[C:32]([C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([O:44]CC)=[O:43])[CH:37]=2)=[O:35])[CH:31]=[CH:30][C:29]=1[OH:47])C>CCCCCC.C(OCC)(=O)C>[C:42]([C:38]1[CH:37]=[C:36]([C:34]([C:32]2[CH:31]=[CH:30][C:29]([O:47][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]3[CH:18]=[CH:17][C:11]4[C:12](=[O:16])[CH2:13][CH2:14][O:15][C:10]=4[C:9]=3[CH2:19][CH2:20][CH3:21])=[C:28]([CH2:27][CH2:26][C:25]([OH:48])=[O:24])[CH:33]=2)=[O:35])[CH:41]=[CH:40][CH:39]=1)([OH:44])=[O:43]

Participants

4

Reactant 2

HCID 147396575-[3-(Ethoxycarbonyl)benzoyl]-2-hydroxybenzenepropanoic acid ethyl esterHCID 19921918HCID 19921918, compound

Product 1

HCID 19922077HCID 19922077, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Starting with 0.275 g (0.78 mmol) of 7-[(5-bromopentyl)oxy]-2,3-dihydro-8-propyl-4H-1-benzopyran-4-one, and 0.286 g (0.77 mmol) of 5-[[3-(ethoxycarbonyl)phenyl]carbonyl]-2-hydroxybenzenepropanoic acid ethyl ester, 5-[(3-carboxyphenyl)carbonyl]-2-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyloxy]benzenepropanoic acid (0.163 g; 52% overall yield) was obtained, as a white solid, mp 122°-128° C. (recrystallized from hexane-ethyl acetate), using the procedure of example 19.

Sources & evidence

ORD record
ord-1e5428ee61c946f4ad7f5c1814cc3d23
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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