Dimethyl Sulfoxide → HCID 88116354, compound

HRID 1862723Notes

Reaction equation

HRID 1862723 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][N:12]([CH:21]1[CH2:25][CH:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]([CH2:32][OH:33])[CH2:22]1)[C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C>ClCCl>[CH3:11][N:12]([CH:21]1[CH2:25][CH:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]([CH:32]=[O:33])[CH2:22]1)[C:13](=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 70026452HCID 70026452, compound

Product 1

HCID 88116354HCID 88116354, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.884 mL, 10.2 mmol) was dissolved in dichloromethane (30 mL) and chilled to −78°. Dimethylsulfoxide (1.44 mL, 10.3 mmol) was added slowly and the solution was aged 15 minutes. A solution of 1-(RS)-(N-(methyl)-N-(benzoyl)amino)-3-(SR)-(hydroxymethyl)4-(SR)-phenylcyclopentane (1.26 g, 4.1 mmol), the higher Rf isomer from Step C, in methylene chloride (3 mL) was added slowly and the solution was aged for one hour. N,N-diisopropylethylamine (7.09 mL, 40.7 mmol) was added to the solution. After aging 10 minutes at −78°, the bath was removed and the solution was warmed to ambient temperature over one hour. The organic layers were washed sequentially with 1N HCl, water and brine, then dried over sodium sulfate and concentrated to afford the crude title compound which was essentially the same as Example 11, Step D.

Workup

  1. temperaturechilled to −78°
  2. waitthe solution was aged for one hour
  3. waitAfter aging 10 minutes at −78°
  4. customthe bath was removed
  5. washThe organic layers were washed sequentially with 1N HCl, water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f74322a422ff4fbdb8cb0921e1ee6721
Source dataset
uspto-grants-2003_03
Patent number
US06538002B1

Reaction notes

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