Dimethyl Sulfoxide → HCID 72574152, compound

HRID 271387Notes

Reaction equation

HRID 271387 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][CH:12]1[CH:17]([O:18][CH2:19][CH:20]([OH:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15][CH:14]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:13]1.C(N(C(C)C)CC)(C)C>ClCCl>[F:11][CH:12]1[CH:17]([O:18][CH2:19][C:20](=[O:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:16][CH2:15][CH:14]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:13]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 72574147HCID 72574147, compound

Product 1

HCID 72574152HCID 72574152, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (0.054 mL, 0.623 mmol) in dichloromethane (10 mL) was cooled to −78° C. Dimethylsulfoxide (0.088 mL, 1.36 mmol) was added dropwise and the reaction mixture was stirred for 5 min. (−) tert-Butyl 3-fluoro-4-(2-hydroxy-2-phenylethoxy)cyclohexylcarbamate (200 mg, 0.567 mmol) was then added as a solution in dichloromethane (1 mL). After 5 min of stirring, diisopropylethylamine (0.494 mL, 2.84 mmol) was added in one portion, the reaction mixture was warmed to room temperature and stirred for 2 h. The reaction mixture was then poured saturated sodium bicarbonate, the layers were separated and the aqueous extracted (4×) with dichloromethane. The combined organic layers were dried with anhydrous magnesium sulfate, filtered and concentrated. Purification by flash column chromatography (hexane: ethyl acetate) gave tert-Butyl 3-fluoro-4-(2-oxo-2-phenylethoxy)cyclohexylcarbamate (175 mg, 88% yield) as a white solid.

Workup

  1. stirringstirred for 2 h
  2. custompoured saturated sodium bicarbonate, the layers were separated
  3. extractionthe aqueous extracted (4×) with dichloromethane
  4. dry with materialThe combined organic layers were dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (hexane: ethyl acetate)

Sources & evidence

ORD record
ord-fe22d000004d43908d5f3c3a9e6fd2b2
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

Loading…