Glyoxylic Acid → HCID 88289825, compound

HRID 1418671Notes

Reaction equation

HRID 1418671 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.O1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][NH2:13].C(OC(=O)/C=N\O[C:21]1[N:22]=[C:23]([NH2:26])[S:24][CH:25]=1)C.[CH:28]1(Br)CCC[CH2:29]1>C(O)C.C(N(CC)CC)C>[CH2:28]([O:5][C:1](=[O:4])/[CH:2]=[N:13]\[O:12][CH:7]1[CH2:11][CH2:10][CH2:9][CH:8]1[C:21]1[N:22]=[C:23]([NH2:26])[S:24][CH:25]=1)[CH3:29]

Participants

7

Reactant 4

HCID 760Glyoxylic AcidHCID 8728BromocyclopentaneHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 88289252HCID 88289252, compound

Product 1

HCID 88289825HCID 88289825, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

The tetrahydropyranyl derivative (as used in Example 3) is prepared by treating the glyoxylic acid derivative described below with O-(tetrahydro-pyran-2-yl)-hydroxyl-amine in the presence of triethylamine in ethanol as depicted below: ##STR7## d) For the preparation of the cyclopentyl derivative the compound A is deprotonated and treated with cyclopentylbromide to form (Z)-2-(aminothiazol-4-yl)cyclopentyl-oxyimino acetic acid ethylester which is then hydrolysed to yield the free acid. The free acid is then reacted in analogy to example 1 to yield the activated acid.

Sources & evidence

ORD record
ord-3c6c0ed19fb044fd9034743cfb61f3a0
Source dataset
uspto-grants-1999_03
Patent number
US05883247

Reaction notes

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