Potassium Carbonate → HCID 22940464, compound

HRID 380226Notes

Reaction equation

HRID 380226 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:15][C@H:16]([OH:32])[C@@H:17]([NH:25]C(=O)C(F)(F)F)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>CO.O>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:15][C@H:16]([OH:32])[C@@H:17]([NH2:25])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 22940467HCID 22940467, compound

Product 1

HCID 22940464HCID 22940464, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

11.75 g (21 mmol) of 1-[4-(pyrazin-2-yl)-phenyl]-4(S)-hydroxy-2-(tert-butoxycarbonyl)amino-5(S)-(trifluoroacetyl)amino-6-phenyl-2-azahexane are suspended in 500 ml of methanol and, at 60° C., 105 ml of a 1M K2CO3 solution in water are added. The mixture is stirred at 75° C. for about 3 hours; the methanol is evaporated off and the residue is extracted with ethyl acetate. The organic phase is washed once each with water and brine and concentrated. The title compound is obtained in the form of orange-brown crystals, which can be recrystallised from ethyl acetate/petroleum ether. M.p.: 146-148° C. TLC: Rf=0.08 (methylene chloride/methanol 10:1). HPLC20-100: tRet=11.23.

Workup

  1. customthe methanol is evaporated off
  2. extractionthe residue is extracted with ethyl acetate
  3. washThe organic phase is washed once each with water and brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f6ba65fc6c4941ed95544bd463de5713
Source dataset
uspto-grants-2001_10
Patent number
US06300519B1

Reaction notes

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