Dimethyl Sulfoxide → HCID 18753603, compound

HRID 1838430Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH:13]([N:26]([CH3:43])[S:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].C(N(CC)CC)C>ClCCl>[CH:12]([CH:13]([N:26]([CH3:43])[S:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])=[O:11]

Participants

Conditions

Temperature: -78 °C

Procedure

Oxalyl cloride (0.51 g, 4.00 mmol) and dimethyl sulfoxide (0.63 g, 8.01 mmol) were dissolved in dichloromethane (10 ml) and the solution was cooled to −78° C. To the solution, a solution of (±)-1-hydroxymethyl-N-methyl-N-(4-phenoxybenzene-sulfonyl)-2-phthalimidoethylamine (1.70 g, 3.64 mmol), the product of (5) above, in dichloromethane (25 ml) was added dropwise with stirring and this was stirred for 30 minutes. Triethylamine (1.84 g, 18.2 mmol) was added dropwise to the mixture and this was stirred at room temperature for 2 hours. To the reaction mixture, ice-water was added and then this was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the desired compound (1.58 g, yield 93%) as a white amorphous solid.

Workup

stirringthis was stirred for 30 minutes
stirringthis was stirred at room temperature for 2 hours
extractionthis was extracted with dichloromethane
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9e80884c6321403f8e95cb30306724f6
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673804B1

Reaction notes

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