Dimethyl Sulfoxide → HCID 131727727, compound

HRID 1433328Notes

Reaction equation

HRID 1433328 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([SiH2:15][O:16][C:17]([CH3:43])([CH3:42])[C@@:18]([NH:38][C:39](=[O:41])[CH3:40])([CH3:37])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([OH:36])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]([F:35])([F:34])[F:33])=[CH:23][CH:22]=1)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([SiH2:15][O:16][C:17]([CH3:43])([CH3:42])[C@@:18]([NH:38][C:39](=[O:41])[CH3:40])([CH3:37])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:36])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]([F:35])([F:33])[F:34])=[CH:23][CH:22]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 131727728HCID 131727728, compound

Product 1

HCID 131727727HCID 131727727, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalylchloride (0.15 mmol) in CH2Cl2 is added at −78° C. first DMSO (0.2 mmol) and then a solution of N-{(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methyl-3-[4-(6,6,6-trifluoro-1-hydroxy-hexyl)-phenyl]-propyl}-acetamide (0.1 mmol) in CH2Cl2. After stirring for 1 h at −78° C., triethylamine (0.7 mmol) is added and the mixture is warmed to RT. Quenching with water is followed by extraction with AcOEt. After drying (MgSO4), the solvent is evaporated.

Workup

  1. temperaturethe mixture is warmed to RT
  2. customQuenching with water
  3. extractionis followed by extraction with AcOEt
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-ccfbb3e35cd04f84ae5b1bbed86d3b74
Source dataset
uspto-grants-2009_11
Patent number
US07612238B2

Reaction notes

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