Pyridine → HCID 67859589, compound

HRID 326180Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:24]C2CCCCO2)[CH:18]([F:23])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:31]C2CCCCO2)[CH2:12][C@@H:11]1O.[N+](=C)=[N-].C1(C)C=CC(S([Cl:52])(=O)=O)=CC=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([OH:24])[CH:18]([F:23])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([OH:31])[CH2:12][C@H:11]1[Cl:52]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1.2 g of (5Z,13E)-(9S,11R,15R,16RS)-9-hydroxy-16-fluoro-11,15-bis(tetrahydropyran-2-yloxy)-5,13-prostadienoic acid methyl ester (prepared from the corresponding acid in methylene chloride with 0.5-molar diazomethane solution at 0° C.), 800 mg of p-toluenesulfonic acid chloride, and 4 ml of pyridine is agitated for 16 hours at 0° C., then for 48 hours at 25° C. The mixture is worked up according to Example 1. Yield: 1.45 g of the 9-tosylate as an oil.

Workup

waitfor 48 hours at 25° C

Sources & evidence

ORD record: ord-c89d12f4835e4c5a9bb7d318fb611a54
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04444788

Reaction notes

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