Triethylamine → Salicylamide

HRID 1077063Notes

Reaction equation

CCCCC[C@H](O)/C=C/[C@@H]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\CCCC(O)=O)[C@@H:12]([OH:23])[CH2:11][C@H:10]1[OH:24].C(OC(Cl)=O)C(C)C.C([N:36](CC)CC)C>>[OH:23][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]([NH2:36])=[O:24]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 62365Isobutyl chloroformate

HCID 5280363Dinoprost

Product 1

HCID 5147Salicylamide

Procedure

Following the procedure of Example 1 but using 0.738 g. of PGF2 α , 0.306 ml. of triethylamine, 0.288 ml. of isobutylchloroformate, and 0.299 g. of o-hydroxybenzamide, there is obtained a crude residue. This residue is subjected to silica gel chromatography, eluting with ethyl acetate-acetone-water (25:75:1). The residue obtained by concentration of selected fractions, 0.296 g., is crystallized from ethyl acetate diluted with 1.5 volumes of hexane as the title compound, white free-flowing crystals, m.p., 98.5°-100.1° C. having Rf 0.55 (TLC on silica gel in ethyl acetate-acetone (1:3)).

Sources & evidence

ORD record: ord-3d2505a6df8f4297a2cda8bc840e05d2
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03959319

Reaction notes

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