Dimethyl Sulfoxide → HCID 60029896, compound

HRID 496399Notes

Reaction equation

HRID 496399 reaction equation
[N:1]1([CH2:6][C@H:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:8][C:9]2[C:10]([CH2:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:36]=[O:37].CS(C)=O>C(O)C>[OH:37][CH2:36][C:2]1[N:1]([CH2:6][C@H:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:8][C:9]2[C:10]([CH2:20][S:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)(=[O:23])=[O:22])=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 712FormaldehydeHCID 10345317HCID 10345317, compound

Product 1

HCID 60029896HCID 60029896, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (S)-6-[2-(1H-imidazol-1-yl)-1-phenylethoxy]-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone (see example 3, 250 mg, 0.51 mmol), paraformaldehyde (1.5 g) and dimethylsulfoxide (6 mL) was stirred at 130° C. for 24 h. The mixture was diluted with ethanol (10 mL), filtered, concentrated, diluted with water (50 mL) and extracted with ethyl acetate (4×10 mL). The combined extracts were washed with water (3×10 mL), dried (brine, Na2SO4), and concentrated. The residue was purified by dry-flash column chromatography (SiO2, 2.5-22.5% 2-propanol-dichloromethane) to give (S)-6-{2-[2-(hydroxymethyl)-1H-imidazol-1-yl]-1-phenylethoxy}-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone as a white solid, 161 mg, 61% yield. NMR spectrum was consistent with structure. MS EI: M+* 517.1816 (M+* 517.1797).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additiondiluted with water (50 mL)
  4. extractionextracted with ethyl acetate (4×10 mL)
  5. washThe combined extracts were washed with water (3×10 mL)
  6. dry with materialdried (brine, Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by dry-flash column chromatography (SiO2, 2.5-22.5% 2-propanol-dichloromethane)

Sources & evidence

ORD record
ord-56fffda3be914e129d0bb0c3e369b7ec
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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