Dimethyl Sulfoxide → HCID 57929392, compound

HRID 1024111Notes

Reaction equation

HRID 1024111 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:17][C:16](=[O:18])[C:15]([OH:19])=[C:14]2[C:20]2[CH:25]=[CH:24][C:23]([CH:26]([OH:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[CH:8][CH:9]=1)=[O:4].CS(C)=O.P([O-])([O-])([O-])=O>C(Cl)Cl>[OH:19][C:15]1[C:16](=[O:18])[CH2:17][C@H:13]([CH2:12][CH2:11][CH2:10][C:7]2[S:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=2)[C:14]=1[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([OH:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1061PhosphateHCID 57929376HCID 57929376, compound

Product 1

HCID 57929392HCID 57929392, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 31 (5 mg, 0.011 mmol), rabbit liver esterase (3 mg, Aldrich), DMSO (50 μL) and pH 7.2 phosphate buffer (0.5 mL) was stirred at room temperature overnight. The reaction was diluted with CH2Cl2 and washed with H2O and brine. The resulting organic solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (0%→30% methanol/dichloromethane) gave the title compound (1 mg, 21%).

Workup

  1. washwashed with H2O and brine
  2. dry with materialThe resulting organic solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography on silica gel (0%→30% methanol/dichloromethane)

Sources & evidence

ORD record
ord-9525c395e0744228b4e33d04d4591819
Source dataset
uspto-grants-2014_05
Patent number
US08722726B2

Reaction notes

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