Diethyl Oxalate → 8-[2-(Benzyloxymethyl)benzofuran-5-carboxamido]-4-oxo-4H-1-benzopyran-2-carboxylic acid

HRID 1603894Notes

Reaction equation

HRID 1603894 reaction equation
C(C1C(O)=C(NC(C2C=CC3OC(COCC4C=CC=CC=4)=CC=3C=2)=O)C=CC=1)(=O)C.C(OCC)(=O)C(OCC)=O.[CH2:42]([O:49][CH2:50][C:51]1[O:52][C:53]2[CH:59]=[CH:58][C:57]([C:60]([NH:62][C:63]3[C:72]4[O:71][C:70]([C:73]([O:75]CC)=[O:74])=[CH:69][C:68](=[O:78])[C:67]=4[CH:66]=[CH:65][CH:64]=3)=[O:61])=[CH:56][C:54]=2[CH:55]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH2:42]([O:49][CH2:50][C:51]1[O:52][C:53]2[CH:59]=[CH:58][C:57]([C:60]([NH:62][C:63]3[C:72]4[O:71][C:70]([C:73]([OH:75])=[O:74])=[CH:69][C:68](=[O:78])[C:67]=4[CH:66]=[CH:65][CH:64]=3)=[O:61])=[CH:56][C:54]=2[CH:55]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 7268Diethyl OxalateHCID 19606326N-(3-acetyl-2-hydroxyphenyl)-2-(benzyloxymethyl)benzofuran-5-carboxamideHCID 19606364ethyl 8-[2-(benzyloxymethyl)benzofuran-5-carboxamido]-4-oxo-4H-1-benzopyran-2-carboxylate

Product 1

HCID 196063338-[2-(Benzyloxymethyl)benzofuran-5-carboxamido]-4-oxo-4H-1-benzopyran-2-carboxylic acid

Procedure

Following the process described in example 1 (point A), starting from N-(3-acetyl-2-hydroxyphenyl)-2-(benzyloxymethyl)benzofuran-5-carboxamide and diethyl oxalate, ethyl 8-[2-(benzyloxymethyl)benzofuran-5-carboxamido]-4-oxo-4H-1-benzopyran-2-carboxylate was prepared which was subsequently hydrolysed according to the process described in example 1 (point M) to yield the title compound as a white solid with melting point 215-218° C. (65% global yield).

Workup

  1. customwas prepared which

Sources & evidence

ORD record
ord-c80e4b8ab5f840fe8016c9da09487413
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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