Diethyl Oxalate → HCID 19606365, compound

HRID 1603911Notes

Reaction equation

[C:1]([C:4]1[C:5]([OH:32])=[C:6]([NH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]3[O:20][CH:19]([CH2:21][CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:18][C:17]=3[C:30]=2[Cl:31])=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[C:33](OCC)(=O)[C:34]([O:36][CH2:37][CH3:38])=[O:35]>>[Cl:31][C:30]1[C:17]2[CH2:18][CH:19]([CH2:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:20][C:16]=2[CH:15]=[CH:14][C:13]=1[C:11]([NH:10][C:6]1[C:5]2[O:32][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:2][C:1](=[O:3])[C:4]=2[CH:9]=[CH:8][CH:7]=1)=[O:12]

Participants

Reactant 2

HCID 7268Diethyl Oxalate

HCID 19606359HCID 19606359, compound

Product 1

HCID 19606365HCID 19606365, compoundYield 61%

Procedure

Following the process described in example 1 (point A), starting from N-(3-acetyl-2-hydroxyphenyl)-4-chloro-2-(3-phenylpropyl)-2,3-dihydrobenzofuran-5-carboxamide and diethyl oxalate, the title compound was prepared, which was purified by chromatography through a silica gel column, eluting with petroleum ether:chloroform, 4:6 (61% yield).

Workup

customwhich was purified by chromatography through a silica gel column
washeluting with petroleum ether

Sources & evidence

ORD record: ord-986e51cab33f439282d24b234ec8e100
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990142

Reaction notes

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