Triethylamine → HCID 178470087, compound

HRID 1093075Notes

Reaction equation

HRID 1093075 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:20]2[NH:21][C:22](=O)[C:23]([OH:31])=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:25]=2)[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:20]2[NH:21][CH2:22][C:23]([O:31][S:34]([CH3:33])(=[O:36])=[O:35])=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:25]=2)[CH2:17][CH2:16][CH:15]([CH2:18][O:19][S:34]([CH3:33])(=[O:36])=[O:35])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 136061329HCID 136061329, compound

Product 1

HCID 178470087HCID 178470087, compoundYield 815.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 2-(1-(benzyloxycarbonylamino)-4-(hydroxymethyl)cyclohexyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (1.85 g, 4.15 mmol) in THF (40 mL) cooled to 0° C. was added methanesulfonyl chloride (0.96 mmol, 12.45 mmol) and triethylamine (1.79 mL, 12.87 mmol). The mixture was allowed to warm to room temperature and stirred for 18 h. The resulting precipitate was filtered off and washed with THF. The filtrate and washings were concentrated to afford an amber oil. A solution of this oil in methanol (10 mL) was treated with K2CO3 (574 mg, 4.15 mmol) at room temperature for 3 h. The mixture was then concentrated and the residue was dissolved in ethyl acetate (200 mL), washed with 1N HCl (100 mL) followed by brine (100 mL), then dried (Na2SO4), filtered and concentrated to give 2.3 g of title compound as a yellow oil. LCMS (M+H)=602.45.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with THF
  3. concentrationThe filtrate and washings were concentrated
  4. customto afford an amber oil
  5. concentrationThe mixture was then concentrated
  6. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  7. washwashed with 1N HCl (100 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e81b67721eaf42ca9336a422de6a6a52
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

Loading…