Dimethyl Sulfoxide → HCID 131722601, compound

HRID 1281203Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]1[CH2:51][O:50][C:13]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])([CH2:14][CH2:15][C@H:16]2[C@H:20]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[CH2:19][C@H:18]([OH:28])[C@@H:17]2[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH:40]([CH3:42])[CH3:41])=[O:38])[O:12]1.C(N(CC)CC)C>ClCCl>[CH2:51]1[CH2:11][O:12][C:13]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])([CH2:14][CH2:15][C@H:16]2[C@H:20]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[CH2:19][C:18](=[O:28])[C@@H:17]2[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH:40]([CH3:42])[CH3:41])=[O:38])[O:50]1

Participants

Conditions

Temperature: -70 °C

Procedure

Oxalyl chloride (2M; 0.45 ml) and DMSO(0.13 ml) were added to dichloromethane (5 ml) which was previously cooled to −70° C. and the mixture was agitated for 15 minutes. The solution of isopropyl (Z)-9-[(1R,2R,3R,5S)-2-(3,3-ethylene dioxydecyl)-5-hydroxy-3-(tetrahydropyranyloxy)cyclopentyl]-7-nonenoate (3-a)(0.350 g) in dichloromethane (7 ml) was dropped into the mixture. The resultant mixture was warmed to −55° C. and agitated for 15 minutes, and then triethylamine (0.25 ml) was added to the mixture. The resultant mixture was warmed to 10° C. over 6 hours. The crude product obtained by the conventional treatment of the reaction mixture was purified on silica gel column to give the titled compound (5-a)[yield:0.311 g(89%)].

Workup

stirringagitated for 15 minutes
customThe crude product obtained by the conventional treatment of the reaction mixture
customwas purified on silica gel column

Sources & evidence

ORD record: ord-71ff16a022cb46a6ba08b1c030ed27ed
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06452039B1

Reaction notes

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