Triethylamine → HCID 54561222, compound

HRID 2227848Notes

Reaction equation

HRID 2227848 reaction equation
[C:1]([O:6][C@@H:7]([C:9]1[NH:14][C:13](=[O:15])[CH:12]=[CH:11][N:10]=1)[CH3:8])(=[O:5])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[C:1]([O:6][C@@H:7]([C:9]1[N:14]=[C:13]([O:15][S:24]([CH3:23])(=[O:26])=[O:25])[CH:12]=[CH:11][N:10]=1)[CH3:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10910803HCID 10910803, compound

Product 1

HCID 54561222HCID 54561222, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of (R)-2-(1-butyryloxy-ethyl)-3H-pyrimidin-4-one (prepared according to the method of Preparation Fourteen, 17.8 g, 97.8 mmol) and triethylamine (9.9 g, 97.8 mmol) in dichloromethane (100 mL) was added methanesulfonyl chloride (11.21 g, 97.8 mmol) dropwise and stirred for 1 h. The mixture was washed successively with saturated aqueous sodium bicarbonate and water, dried over magnesium sulfate and filtered. The filtrate was evaporated to give the title compound as an oil, 24.1 g (94%). 1H NMR (CDCl3, 300 MHz) δ0.99 (t, 3H), 1.54 (d, 3H), 1.68 (m, 2H), 2.48 (t, 2H), 3.81 (s, 3H), 5.54 (q, 1H), 6.38 (d, 1H), 8.24 (d, 1H); MS (CI) 261 (MH+); [α]D +28.8 (c 1.0, MeOH).

Workup

  1. washThe mixture was washed successively with saturated aqueous sodium bicarbonate and water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d974228422d34c02bdfdc45690bcb5a7
Source dataset
uspto-grants-2002_07
Patent number
US06414149B1

Reaction notes

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