Triethylamine → 4-Hydroxybenzamide

HRID 1288071Notes

Reaction equation

CCCCC[C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/C=C\CCCC(O)=O)[C@@H](O)C[C@H:10]1[OH:24].C(OC(Cl)=O)C(C)C.C([N:36](CC)CC)C>>[OH:25][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH2:36])=[O:24])=[CH:13][CH:14]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 62365Isobutyl chloroformate

HCID 5280363Dinoprost

Product 1

HCID 650524-Hydroxybenzamide

Procedure

Following the procedure of Example 1 but using 0.738 g. of PGF2α, 0.347 ml. of triethylamine, 0.326 ml. of isobutylchloroformate, and 0.433 g. of p-hydroxybenzamide, there is obtained a crude residue. This residue is subjected to silica gel chromatography, eluting with ethyl acetate-acetone (3:7). The residue obtained by concentration of selected fractions, 0.455 g., is crystallized from acetone diluted with an equal volume of acetonitrile as the title compound, white, free-flowing crystals, m.p. 129.5°-130.8° C., having Rf 0.32 (TLC on silica gel in ethyl acetate-acetone (3:7)).

Sources & evidence

ORD record: ord-e37672eb9c3e4a68a435b6718d381742
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03987067

Reaction notes

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