HCID 19921918, compound → HCID 19922077, compound

HRID 327945Notes

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]=[CH:32][CH:31]=[C:30]([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])[C:29]=1O)C.CCCCCC.C(OCC)(=[O:57])C>>[C:42]([C:38]1[CH:37]=[C:36]([C:34]([C:30]2[CH:31]=[CH:32][C:33]([O:57][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:24])=[O:48])[CH:29]=2)=[O:35])[CH:41]=[CH:40][CH:39]=1)([OH:44])=[O:43]

Participants

Reactant 3

HCID 19921918HCID 19921918, compound

HCID 21226206Ethyl acetate hexane

HCID 86747451HCID 86747451, compound

Product 1

HCID 19922077HCID 19922077, compoundYield 52%

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-1a774b170e8c40c59355cfff736c9bae
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05273999

Reaction notes

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