Dimethyl Sulfoxide → HCID 9871161, compound

HRID 1061682Notes

Reaction equation

HRID 1061682 reaction equation
CS(C)=O.CO.C(=O)=O.C(Cl)(=O)C(Cl)=O.[C:16]([N:19]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:22]([CH2:31][C:32]([NH:34][CH:35]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:36]([OH:41])[C:37]([F:40])([F:39])[F:38])=[O:33])[C:21](=[O:49])[CH:20]1[CH:50]([CH3:52])[CH3:51])(=[O:18])[CH3:17]>C(Cl)Cl.C(OCC)(=O)C.C(N(CC)CC)C>[C:16]([N:19]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:22]([CH2:31][C:32]([NH:34][CH:35]([CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:36](=[O:41])[C:37]([F:40])([F:39])[F:38])=[O:33])[C:21](=[O:49])[CH:20]1[CH:50]([CH3:52])[CH3:51])(=[O:18])[CH3:17]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 9806620HCID 9806620, compoundHCID 21973728Carbon dioxide methanol

Product 1

HCID 9871161HCID 9871161, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of dimethyl sulfoxide (0.26 ml) in anhydrous methylene chloride (4.0 ml) is cooled with methanol/dry ice, oxalyl chloride (0.16 ml) is added to the solution, and the mixture is stirred for 10 minutes. To the mixture is added a solution of (2RS,3RS)-3-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-2-hydroxy-4-phenyl-1,1,1-trifluorobutane (0.75 ml, Compound No. 2-1) in anhydrous methylene chloride (3.0 ml). The temperature is raised to 0° C., triethylamine (0.75 ml) is added thereto, and the whole is stirred for one hour. Ethyl acetate is added to the reaction mixture, the whole is washed with a saturated aqueous ammonium chloride solution and saturated brine successively, and the organic layer is dried over anhydrous magnesium sulfate. The organic layer is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled compound (154 mg).

Workup

  1. additionis added to the solution
  2. stirringthe whole is stirred for one hour
  3. washthe whole is washed with a saturated aqueous ammonium chloride solution and saturated brine successively
  4. dry with materialthe organic layer is dried over anhydrous magnesium sulfate
  5. concentrationThe organic layer is concentrated under reduced pressure
  6. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dbbe9acb8eb14f349735c333eaf48523
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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