Dimethyl Sulfoxide → HCID 86600810, compound

HRID 553100Notes

Reaction equation

HRID 553100 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16](=[O:35])[NH:17][CH:18]([C:22](=[O:34])[NH:23][C:24]1[N:25]=[CH:26][N:27]([C:29]([CH3:33])([CH3:32])[CH2:30][OH:31])[CH:28]=1)[CH2:19][CH2:20][CH3:21])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([O:15][C:16](=[O:35])[NH:17][CH:18]([C:22](=[O:34])[NH:23][C:24]1[N:25]=[CH:26][N:27]([C:29]([CH3:33])([CH3:32])[CH:30]=[O:31])[CH:28]=1)[CH2:19][CH2:20][CH3:21])([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67163383HCID 67163383, compound

Product 1

HCID 86600810HCID 86600810, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of oxalyl chloride (1.2 mL, 14.1 mmol) in 110 mL of methylene chloride at −78° C. is added DMSO (2.2 mL, 30.6 mmol) dropwise. The reaction is stirred for 20 min. and {1-[1-(2-Hydroxy-1,1-dimethyl-ethyl)-1H-imidazol-4-ylcarbamoyl]-butyl}-carbamic acid tert-butyl ester (4.2 g, 11.8 mmol) is added in 10 mL of methylene chloride. The reaction is stirred for 1 h, triethylamine (8.2 mL, 58.9 mmol) is added, and the reaction warmed to 0° C. for 20 min. The reaction is quenched with 100 mL of sodium bicarbonate, extracted with methylene chloride, dried, and concentrated to afford the title compound (4.5 g): MS m/z 353.2 (M+1).

Workup

  1. stirringThe reaction is stirred for 1 h
  2. customThe reaction is quenched with 100 mL of sodium bicarbonate
  3. extractionextracted with methylene chloride
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1d030d3e74524587a09e4d43788637ee
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

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