Methanesulfonic Acid → HCID 59006381, compound

HRID 2378947Notes

Reaction equation

HRID 2378947 reaction equation
CO[CH:3](OC)[CH2:4][N:5]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])=[O:7].CS(O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>O.C(=O)(O)[O-].[Na+].O1CCOCC1>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:8]1[CH:3]=[CH:4][N:5]([CH:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH2:21]2)[C:6]1=[O:7]

Participants

8

Reactant 4

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 59006376HCID 59006376, compound

Product 1

HCID 59006381HCID 59006381, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl 4-(1-(2,2-dimethoxyethyl)-3-(2-fluorophenyl)ureido)piperidine-1-carboxylate (1.39 g, 3267 μmol) was dissolved in a mixture of water (8.0 ml) and methanesulfonic acid (8.0 ml, 123281 μmol). Mixture was heated to 100° C. and held for 15 minutes. Mixture was cooled to room temperature. Reaction was neutralized with sodium carbonate (6.15 g, 58025 μmol). Mixture was diluted with aqueous sodium bicarbonate. 1,4-Dioxane (10 ml) was added to the mixture followed by di-tert-butyl dicarbonate (880 mg, 4032 μmol). Reaction stirred vigorously at room temperature for 3 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 clear colorless oil in 64% yield. MS (M−C4H10O+H)−=288.1.

Workup

  1. temperatureMixture was cooled to room temperature
  2. customReaction
  3. customReaction
  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-29f7d30174af48598432fc913df5d2e2
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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