Dimethyl Sulfoxide → HCID 86746994, compound

HRID 1463933Notes

Reaction equation

HRID 1463933 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([C:41]([F:46])([F:45])[CH2:42][CH2:43][CH3:44])[CH2:13][CH2:14][CH2:15][C@H:16]1[C@H:20]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH2:19][C@H:18]([OH:28])[C@@H:17]1[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH:38](C)C)=[O:36].C(N(CC)CC)C>C(Cl)Cl>[F:46][C:41]([F:45])([CH2:42][CH2:43][CH3:44])[C:12](=[O:11])[CH2:13][CH2:14][CH2:15][C@H:16]1[C@H:20]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH2:19][C:18](=[O:28])[C@@H:17]1[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 131718385HCID 131718385, compound

Product 1

HCID 86746994HCID 86746994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride in methylene chloride (2M, 3.5 ml) was cooled to -78° C., followed by addition of DMSO (1.1 ml). A solution of the compound (18) (0.906 g) in methylene chloride (11 ml) was added dropwise. The resultant mixture was stirred at the range of -35 to -25° C. for 1.5 hours, and triethylamine (2.lml) was added dropwise. After 20 minutes, 1Nhydrochloric acid was added. The crude product obtained after the usual work-up was subjected to silicagel column chromatography to give the titled compound (19).

Workup

  1. addition1Nhydrochloric acid was added
  2. customThe crude product obtained after the usual work-up

Sources & evidence

ORD record
ord-23ab12d84c4b4357ac1fb3a836ac4c95
Source dataset
uspto-grants-1994_04
Patent number
US05302617

Reaction notes

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