Methanesulfonic Acid → HCID 59006339, compound

HRID 2378935Notes

Reaction equation

HRID 2378935 reaction equation
CO[CH:3](OC)[CH2:4][N:5]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7].CS(O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>O.O1CCOCC1>[O:7]=[C:6]1[N:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:3]=[CH:4][N:5]1[CH:15]1[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:19][CH2:20]1

Participants

8

Reactant 5

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 59006394HCID 59006394, compound

Product 1

HCID 59006339HCID 59006339, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl 4-(1-(2,2-dimethoxyethyl)-3-phenylureido)piperidine-1-carboxylate (1.29 g, 3.17 mmol) was dissolved in a mixture of water (5 ml) and methanesulfonic acid (5 ml, 77 mmol). Reaction was heated to 100° C. and held with stirring for 20 minutes. Mixture was cooled to room temperature. Sodium carbonate (3.75 g, 35.4 mmol) was slowly added to the mixture. Mixture was made basic with aqueous sodium bicarbonate. 1,4-Dioxane (20 ml) was added to the mixture followed by di-tert-butyl dicarbonate (1.0 g, 4.58 mmol). Mixture stirred at room temperature for 18 hours. Reaction was quenched with aqueous ammonium chloride. Material was extracted twice with ethyl acetate and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Silica gel chromatography eluting ethyl acetate-hexanes afforded the title compound as white solid in 59% yield. MS (M−C5H8O2+H)+=244.2.

Workup

  1. customReaction
  2. temperatureMixture was cooled to room temperature
  3. stirringMixture stirred at room temperature for 18 hours
  4. customReaction
  5. customwas quenched with aqueous ammonium chloride
  6. extractionMaterial was extracted twice with ethyl acetate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. washSilica gel chromatography eluting ethyl acetate-hexanes

Sources & evidence

ORD record
ord-f0f9d172e91b4b70be4022ab77fb507a
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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