Triethylamine → 4-Hydroxybenzamide

HRID 597273Notes

Reaction equation

CCCC[CH2:5][C@H:6]([OH:24])/[CH:7]=C/[C@@H]1[C@@H](CCCCCCC(O)=O)C(=O)C=C1.[CH2:25]([O:29]C(Cl)=O)[CH:26]([CH3:28])[CH3:27].C([N:35](CC)CC)C>>[OH:24][C:6]1[CH:7]=[CH:27][C:26]([C:25]([NH2:35])=[O:29])=[CH:28][CH:5]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 62365Isobutyl chloroformate

HCID 5281912Pga1

Product 1

HCID 650524-Hydroxybenzamide

Procedure

Following the procedure of Example 1 but using 0.506 g. of PGA1 0.250 ml. of triethylamine, 0.236 ml. of isobutylchloroformate, and 0.412 g. of p-hydroxybenzamide there is obtained a crude residue. This residue is subjected to silica gel chromatography, eluting with chloroform-acetonitrile (6:4). The residue obtained by concentration of selected fractions, 0.260 g., an oil, as the title compound, having RfO.5 (TLC on silica gel in chloroform-acetonitrile (3:2)).

Sources & evidence

ORD record: ord-8a555b4e21d24cb1b0a6ed1f38151930
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04013693

Reaction notes

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