Triethylamine → HCID 178470088, compound

HRID 1093068Notes

Reaction equation

HRID 1093068 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:19]2[NH:20][CH2:21][C:22]([OH:30])=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:24]=2)[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33].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:19]2[NH:20][CH2:21][C:22]([O:30][S:32]([CH3:31])(=[O:34])=[O:33])=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:24]=2)[CH2:17][CH2:16][CH:15]([O:18][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 178470043HCID 178470043, compound

Product 1

HCID 178470088HCID 178470088, compoundYield 853.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 2-(1-(benzyloxycarbonylamino)-4-hydroxycyclohexyl)-5-hydroxy-1,6-dihydropyrimidine-4-carboxylate (1.75 g, 4.05 mmol) in THF (25 mL) was added methanesulfonyl chloride (0.94 mmol, 12.17 mmol) and triethylamine (1.7 mL, 12.75 mmol) at 5° C. and the mixture stirred at room temperature for 18 h. The resulting white 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 (20 mL) was treated with K2CO3 (560 mg, 4.05 mmol) at room temperature for 3 h. The mixture was then concentrated and the residue dissolved in ethyl acetate (200 mL), washed with 1N HCl (100 mL) followed by brine (100 mL) and then dried (Na2SO4), filtered and concentrated to give 2.3 g of the title compound as an amber oil, which was used in the next step without further purification. LCMS (M+H)=588.41.

Workup

  1. filtrationThe resulting white 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 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-95abd31076a64cd5bd4c1473ad32cae6
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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