Acetic Acid → HCID 70416995, compound

HRID 1105648Notes

Reaction equation

[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17](=[O:47])[CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH2:23][C@@H:24]2[C@@H:28]([S:29][CH2:30][C:31]([OH:38])([CH3:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:27]([O:39]C3CCCCO3)[CH2:26][CH:25]2[OH:46])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC1C=CC(OC(=O)C([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)CCC)=CC=1)(=O)C1C=CC=CC=1.[H-].[Na+].C(O)(=O)C>O.C1COCC1>[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17](=[O:47])[CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH2:23][C@@H:24]2[C@@H:28]([S:29][CH2:30][C:31]([OH:38])([CH3:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:27]([OH:39])[CH2:26][CH:25]2[OH:46])=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

0.25 g. of 9,15-dihydroxy-15-methyl-11-tetrahydropyranyloxy-13-thia-5-prostenoic acid p-benzoylaminophenyl ester (obtainable by the reaction of 2-(2-hydroxy-2-methylheptylthio)-5-hydroxy-3-tetrahydropyranyloxy-acetaldehyde lactol with triphenylphosphoniopentanoic acid p-benzoylaminophenyl ester in the presence of 2 moles of NaH) is stirred for 5 hours at 45° C. in 7 ml. of a mixture of acetic acid, THF and water (3:1:1). The solvent is distilled off, and after chromatographic purification of the residue (silica gel/ethyl acetate), 9,11,15-trihydroxy-15-methyl-13-thia-5-prostenoic acid p-benzoylaminophenyl ester is obtained.

Workup

distillationThe solvent is distilled off
customafter chromatographic purification of the residue (silica gel/ethyl acetate)

Sources & evidence

ORD record: ord-4380c70c3a06495e805bac85f0a66bc1
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04309441

Reaction notes

Loading…