Dimethyl Sulfoxide → HCID 18791391, compound

HRID 1005605Notes

Reaction equation

HRID 1005605 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:58]=[CH:57][CH:56]=[CH:55][C:24]=1[C:25]([NH:27][C:28]1[CH:52]=[CH:51][C:31]([C:32]([N:34]([CH3:50])[C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:36]=2[O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][OH:49])=[O:33])=[CH:30][C:29]=1[O:53][CH3:54])=[O:26])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl.O>[C:11]([O:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:58]=[CH:57][CH:56]=[CH:55][C:24]=1[C:25]([NH:27][C:28]1[CH:52]=[CH:51][C:31]([C:32]([N:34]([CH3:50])[C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:36]=2[O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH:48]=[O:49])=[O:33])=[CH:30][C:29]=1[O:53][CH3:54])=[O:26])=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18791397HCID 18791397, compound

Product 1

HCID 18791391HCID 18791391, compoundYield 121.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a solution of oxalyl chloride (95 mg) in dichloromethane (10 ml) was added dimethyl sulfoxide (117 mg) dropwise at -78° C. The mixture was warmed to -15° C. and a solution of 4-[2-(3-tert-butoxycarbonylaminoprop-1-yl)oxybenzoyl]amino-3-methoxy-N-methyl-N-[2-(6-hydroxyhex-1-yl)oxy-4-methylphenyl]benzamide (450 mg) in dichloromethane (10 ml) was added thereto. After being stirred at the same temperature for 10 minutes, to the reaction mixture was added triethylamine (343 mg) and stirred at the same temperature for 5 minutes. The resulting solution was warmed to ambient temperature and poured into water. The mixture was extracted with chloroform (15 ml×3) and the organic layer was washed with brine. The solution was dried over magnesium sulfate and the solvent was evaporated to give 4-[2-(3-tert-butoxycarbonylaminoprop-1-yl)oxybenzoyl]amino-3-methoxy-N-methyl-N-[2-(5-formylpent-1-yl)oxy-4-methylphenyl]benzamide (546 mg)

Workup

  1. stirringstirred at the same temperature for 5 minutes
  2. temperatureThe resulting solution was warmed to ambient temperature
  3. extractionThe mixture was extracted with chloroform (15 ml×3)
  4. washthe organic layer was washed with brine
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4e9236e4bc3c469bae88f9976417438a
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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