Methanesulfonyl chloride → HCID 58962310, compound

HRID 1365734Notes

Reaction equation

HRID 1365734 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:14]2([O:18][CH2:19][CH2:20][OH:21])[CH2:17][CH2:16][CH2:15]2)[NH:9][C:10](=[O:13])[C:11]=1[OH:12])=[O:5])[CH3:2].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>O1CCCC1>[CH3:22][S:23]([N:9]1[C:10](=[O:13])[C:11]([O:12][S:23]([CH3:22])(=[O:25])=[O:24])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=[C:8]1[C:14]1([O:18][CH2:19][CH2:20][O:21][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:15][CH2:16][CH2:17]1)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 136000856HCID 136000856, compound

Product 1

HCID 58962310HCID 58962310, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cold (0° C.) solution of 5-hydroxy-2-[1-(2-hydroxy-ethoxy)-cyclobutyl]-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (7.23 g, 25 mmol) in anhydrous tetrahydrofuran was treated with methanesulfonylchloride (Aldrich) by dropwise addition. The solution was warmed to room temperature and stirred for 4 hrs. The reaction was concentrated in-vacuo, and the crude product was dissolved in ethyl acetate (75 mL) and washed with saturated sodium bicarbonate solution. The organic solution was dried (sodium sulfate), filtered to remove solids, and concentrated in vacuo to give the title compound as a brown oil. 1H NMR (500 MHz, CDCl3) δ: 4.49 (2H, q, J=7.0 Hz), 4.35-4.38 (2H, m), 3.93-4.00 (1H, m), 3.66-3.67 (3H, s), 3.62-3.65 (2H, m), 3.44-3.46 (3H, s), 3.05-3.07 (3H, s), 2.74-2.82 (1H, m), 2.60-2.67 (2H, m), 2.41-2.49 (2H, m), 1.43 (3H, t, J=7.0 Hz). LCMS (M+H): 532.94.

Workup

  1. concentrationThe reaction was concentrated in-vacuo
  2. dissolutionthe crude product was dissolved in ethyl acetate (75 mL)
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialThe organic solution was dried (sodium sulfate)
  5. filtrationfiltered
  6. customto remove solids
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0b1e4e5bbb546e5b47169f90cf2b8bc
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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