Water → HCID 66726901, compound

HRID 2366058Notes

Reaction equation

HRID 2366058 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C@H:10]([CH2:13]OS(C)(=O)=O)[O:9][C:8]=2[CH:19]=1)([O-:3])=[O:2].C([O-])(O)=O.[Na+].Cl.[NH:26]1[CH2:31][CH2:30][CH2:29][C@H:28]([C:32]2[CH:33]=[C:34]([OH:38])[CH:35]=[CH:36][CH:37]=2)[CH2:27]1.O>CN(C=O)C.C(#N)C.CCCCCCC.CCOC(C)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C@H:10]([CH2:13][N:26]3[CH2:31][CH2:30][CH2:29][C@H:28]([C:32]4[CH:33]=[C:34]([OH:38])[CH:35]=[CH:36][CH:37]=4)[CH2:27]3)[O:9][C:8]=2[CH:19]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 12937951HCID 12937951, compoundHCID 86644730HCID 86644730, compound

Product 1

HCID 66726901HCID 66726901, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

Methanesulfonic acid (R)-7-nitro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester (0.98 mmol, 0.28 g) was dissolved in the mixture of DMF (2.8 ml) and acetonitrile (2.8 ml). NaHCO3 (2.92 mmol, 0.25 g) and (R*)-3-(piperidin-3-yl)phenol hydrochloride was added. The mixture was refluxed 4 h and after cooling water (15 ml) was added. The water phase was extracted twice with ethyl acetate and washed with water and brine. Evaporation to dryness gave 0.36 g of the crude product. Flash chromatography, using heptane/EtOAc as eluent and crystallisation (CHCl3) gave 83 mg of the desired product.

Workup

  1. temperatureThe mixture was refluxed 4 h
  2. additionwas added
  3. extractionThe water phase was extracted twice with ethyl acetate
  4. washwashed with water and brine
  5. customEvaporation to dryness
  6. customgave 0.36 g of the crude product
  7. customcrystallisation (CHCl3)

Sources & evidence

ORD record
ord-244c7f94533e4f6388d9eee9521b4b7f
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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