Potassium Carbonate → HCID 67267943, compound

HRID 2378081Notes

Reaction equation

HRID 2378081 reaction equation
N[C:2]1[N:6]=[C:5]([N:7]2[CH2:12][CH2:11][CH2:10][CH:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8]2)[N:4]([CH2:21][C:22]#[C:23][CH3:24])[C:3]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26].N([O-])=O.[Na+].[PH2](O)=O.C(=O)([O-])[O-].[K+].[K+]>Cl.O>[C:17]([O:16][C:14]([NH:13][CH:9]1[CH2:10][CH2:11][CH2:12][N:7]([C:5]2[N:4]([CH2:21][C:22]#[C:23][CH3:24])[C:3]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:2][N:6]=2)[CH2:8]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 4124402Phosphinic AcidHCID 23668193Sodium NitriteHCID 67268813HCID 67268813, compound

Product 1

HCID 67267943HCID 67267943, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3.00 g ethyl 5-amino-2-(3-tert-butoxycarbonylamino-piperidin-1-yl)-3-(but-2-ynyl)-3H-imidazole-4-carboxylate in 36 ml 2 M hydrochloric acid is cooled to 0° C. To this is added a solution of 0.60 g sodium nitrite in 2 ml of water and the reaction mixture is stirred for 1 h at 0° C. Then 8.4 ml hypophosphorous acid are added and the mixture is stirred for a further 14 h at 0° C. Then the reaction mixture is added to ice-cooled aqueous potassium carbonate solution and extracted with dichloromethane. The organic extracts are dried over sodium sulphate and evaporated down. The residue is dissolved in 8 ml dichloromethane, and 1.62 g di-tert-butyl carbonate are added. The solution is stirred for 2 h at ambient temperature, then evaporated to dryness and chromatographed on silica gel (cyclohexane/ethyl acetate 7:3->1:1).

Workup

  1. stirringthe mixture is stirred for a further 14 h at 0° C
  2. additionThen the reaction mixture is added to ice-
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic extracts are dried over sodium sulphate
  5. customevaporated down
  6. dissolutionThe residue is dissolved in 8 ml dichloromethane
  7. addition1.62 g di-tert-butyl carbonate are added
  8. stirringThe solution is stirred for 2 h at ambient temperature
  9. customevaporated to dryness
  10. customchromatographed on silica gel (cyclohexane/ethyl acetate 7:3->1:1)

Sources & evidence

ORD record
ord-3c49e5d03ef74388bc4a2ee687b1224a
Source dataset
uspto-grants-2008_12
Patent number
US07470716B2

Reaction notes

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