Diisopropylamine → 11alpha,15-Dihydroxy-15-methyl-9-oxo-13-thia-5-prostenoic acid p-benzoylaminophenyl ester

HRID 1105644Notes

Reaction equation

HRID 1105644 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH2:23][C:24]2[C:28](=[O:29])[CH2:27][CH:26]([OH:30])[CH:25]=2)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:32][C:33]([CH3:41])([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:34][SH:35].C(NC(C)C)(C)C>>[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH2:23][C@@H:24]2[C@@H:25]([S:35][CH2:34][C:33]([OH:32])([CH3:41])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C@H:26]([OH:30])[CH2:27][C:28]2=[O:29])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 7912DiisopropylamineHCID 135068602-Methyl-1-sulfanylheptan-2-OLHCID 571897907-(3-Hydroxy-5-oxo-1-cyclopenten-1-yl)-hept-5-enoic acid p-benzoylaminophenyl ester

Product 1

HCID 7055413911alpha,15-Dihydroxy-15-methyl-9-oxo-13-thia-5-prostenoic acid p-benzoylaminophenyl ester

Procedure

Analogously to Example 5, by reaction of 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-hept-5-enoic acid p-benzoylaminophenyl ester with 2-hydroxy-2-methyl-heptanethiol in the presence of diisopropylamine, 11α,15-dihydroxy-15-methyl-9-oxo-13-thia-5-prostenoic acid p-benzoylaminophenyl ester is obtained.

Sources & evidence

ORD record
ord-8b11e128573846898c3a0c8113c8a24b
Source dataset
uspto-grants-1982_01
Patent number
US04309441

Reaction notes

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