Dimethyl Sulfoxide → HCID 57929392, compound

HRID 2201957Notes

Reaction equation

HRID 2201957 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-0718d4b33b1341a68fea36118d6bd8e8
Source dataset
uspto-grants-2016_06
Patent number
US09365485B2

Reaction notes

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