Dimethyl Sulfoxide → HCID 178455320, compound

HRID 1873594Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:18][C@@H:19]1[CH2:24][CH2:23][C@H:22]([CH2:25][OH:26])[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[Si:11]([O:18][C@@H:19]1[CH2:20][CH2:21][C@H:22]([CH:25]=[O:26])[CH2:23][CH2:24]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: -78 °C

Procedure

16.4 g (129.47 mmol) oxalyl chloride are dissolved in 600 ml of dichloromethane and cooled to −78° C. 20.2 g (258.95 mmol) of dimethyl sulfoxide are then slowly added dropwise. The mixture is stirred for 5 min. After addition of a solution of 21.1 g (86.32 mmol) of the compound from Example 53A in 200 ml of dichloromethane the mixture is stirred at −78° C. for 1 h. 60 ml (431.58 mmol) of triethylamine are then slowly added dropwise. Over a period of one hour, the reaction mixture is then warmed to RT, and 500 ml of saturated aqueous sodium bicarbonate solution are then added. The phases are separated, the organic phase is dried over sodium sulfate and the solvent is removed on a rotary evaporator. The residue is purified chromatographically on silica gel 60 (mobile phase: gradient petroleum ether→petroleum ether/ethyl acetate 9:1).

Workup

stirringis stirred at −78° C. for 1 h
waitOver a period of one hour
temperaturethe reaction mixture is then warmed to RT
customThe phases are separated
dry with materialthe organic phase is dried over sodium sulfate
customthe solvent is removed on a rotary evaporator
customThe residue is purified chromatographically on silica gel 60 (mobile phase: gradient petroleum ether→petroleum ether/ethyl acetate 9:1)

Sources & evidence

ORD record: ord-1c4f3cd8115940508540c4a986214f97
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304412B2

Reaction notes

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