p-Toluenesulfonic acid → HCID 178467424, compound

HRID 1169865Notes

Reaction equation

HRID 1169865 reaction equation
[OH:1][C@H:2]([C:9]1[N:10]=[C:11]([C:14](=[O:16])[CH3:15])[NH:12][CH:13]=1)[C@H:3]([OH:8])[C@H:4]([OH:7])[CH2:5][OH:6].[C:17]1(C)[CH:22]=CC(S(O)(=O)=O)=C[CH:18]=1.CO[C:30](OC)([CH3:32])[CH3:31]>ClC(Cl)C.ClCCl>[CH3:18][C:17]1([CH3:22])[O:8][C@H:3]([C@H:4]2[CH2:5][O:6][C:30]([CH3:32])([CH3:31])[O:7]2)[C@@H:2]([C:9]2[N:10]=[C:11]([C:14](=[O:16])[CH3:15])[NH:12][CH:13]=2)[O:1]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 178467425HCID 178467425, compound

Product 1

HCID 178467424HCID 178467424, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

1-[4-((1R,2S,3R)-1,2,3,4-Tetrahydroxy-butyl)-1H-imidazol-2-yl]-ethanone (18 g, 78.3 mmol) was suspended in dichloroethane (160 ml) and 2,2-dimethoxy propane (160 ml). 4-toluenesulfonic acid (3 g) was added and the mixture stirred at 70° C. for 18 hours. The reaction was diluted with dichloromethane and washed with water, 5% bicarbonate, brine and then dry loaded onto SiO2. Purification by flash chromatography (hexane/ethyl acetate) afforded 1-(4-((4S,4′R,5R)-2,2,2′,2′-tetramethyl-4,4′-bi(1,3-dioxolan)-5-yl)-1H-imidazol-2-yl)ethanone as a colorless oil (18.8 g, 60.6 mmol, 77%; M+H calc: 311.4, obs: 311.3).

Workup

  1. washwashed with water, 5% bicarbonate, brine
  2. customdry
  3. customPurification by flash chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5a028d77229742858afb33d3fafdb0d5
Source dataset
uspto-grants-2010_11
Patent number
US07825150B2

Reaction notes

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