Hydrochloric Acid → HCID 66588882, compound

HRID 1093063Notes

Reaction equation

HRID 1093063 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH:13]([CH:27]1[CH2:31][CH2:30][CH:29]([CH2:32]O)[CH2:28]1)[C:14]1[NH:15][C:16](=[O:26])[C:17]([OH:25])=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1)[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(OC(N(C(C1CCC(COS(C)(=O)=O)C1)C1N(S(C)(=O)=O)C(=O)C(OS(C)(=O)=O)=C(C(OCC)=O)N=1)C)=O)C1C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl>C1COCC1.CN(C=O)C.O>[CH2:1]([O:8][C:9]([N:11]([CH3:12])[C:13]12[CH2:32][CH:29]([CH2:30][CH2:31][CH2:27]1)[CH2:28][N:15]1[C:16](=[O:26])[C:17]([OH:25])=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=[C:14]21)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 86634932HCID 86634932, compoundHCID 136061318HCID 136061318, compound

Product 1

HCID 66588882HCID 66588882, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To ethyl 2-(((benzyloxycarbonyl)(methyl)amino)(3-(hydroxymethyl)cyclopentyl)methyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (0.235 g, 0.511 mmol)in THF (30 mL) at 0° C. was added triethylamine (0.214 mL, 1.53 mmol) and methanesulfonyl chloride (0.119 mL, 1.53 mmol). The reaction mixture was stirrer at 23° C. for 3 hours. H2O (50 mL) was then added and the reaction mixture extracted with ethyl acetate (3×50 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo. LCMS (+ESI, M+H+) m/z 694. To the crude ethyl 2-(((benzyloxycarbonyl)(methyl)amino)(3-((methylsulfonyloxy)methyl)cyclopentyl)methyl)-1-(methylsulfonyl)-5-(methylsulfonyloxy)-6-oxo-1,6-dihydropyrimidine-4-carboxylate (0.252 g, 0.363 mmol) dissolved in DMF (40 mL) was added Cs2CO3 (0.590 g, 1.816 mmol). The reaction mixture was stirred at 80° C. for 12 hours. HCl (1N, 40 ml) was added and the organic material was extracted with ethyl acetate (3×30 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to afford the title compound. LCMS (+ESI, M+H+) m/z 442.

Workup

  1. customat 23° C.
  2. customfor 3 hours
  3. extractionthe reaction mixture extracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. extractionthe organic material was extracted with ethyl acetate (3×30 mL)
  7. dry with materialThe combined organic fractions were dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0fb223e5b424423ba9479e18da4ed63
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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