Methyl N-(triethylammoniosulfonyl)carbamate → HCID 68951933, compound

HRID 1453849Notes

Reaction equation

HRID 1453849 reaction equation
[NH2:1][C:2]([CH:4]1[N:9]2[N:10]=[C:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:8]2[C:7](=[O:26])[N:6]([CH3:27])[CH2:5]1)=O.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH2:14]([O:13][C:12]1[C:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:10][N:9]2[CH:4]([C:2]#[N:1])[CH2:5][N:6]([CH3:27])[C:7](=[O:26])[C:8]=12)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamate2×HCID 68954171HCID 68954171, compound

Product 1

HCID 68951933HCID 68951933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethyl 7-aminocarbonyl-3-benzyloxy-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (273 mg, 0.733 mmol) in anhydrous THF under an atmosphere of nitrogen was added Burgess reagent ((methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt, 349 mg, 1.47 mmol). The reaction was stirred at room temperature for 2 hours and then heated to 50° C. for 45 minutes. Additional Burgess reagent (4.89 g, 10.26 mmol) was added in portions and the reaction was heated to 60° C. overnight. The solvent was removed in vacuo, and the resulting residue was partitioned between saturated aqueous NH4Cl and EtOAc. The layers were separated and the aqueous was extracted twice more with EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to afford the title product. 1H NMR (400 MHz, d6-DMSO) δ 7.49-7.47 (m, 2H), 7.40-7.31 (m, 3H), 6.23 (t, J=4.0 Hz, 1H), 5.23 (dd, J=10.8, 24.6 Hz, 2H), 4.33-4.23 (m, 3H), 4.13 (dd, J=3.8, 13.8 Hz, 1H), 3.09 (s, 3H), 1.27 (t, J=7.2 Hz, 3H); ES MS (M+H)=355.

Workup

  1. temperatureheated to 50° C. for 45 minutes
  2. temperaturethe reaction was heated to 60° C. overnight
  3. customThe solvent was removed in vacuo
  4. customthe resulting residue was partitioned between saturated aqueous NH4Cl and EtOAc
  5. customThe layers were separated
  6. extractionthe aqueous was extracted twice more with EtOAc
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ff917bacfa84c9786905cedfe2223c5
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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