Ammonia → HCID 10506677, compound

HRID 400307Notes

Reaction equation

HRID 400307 reaction equation
[CH:1]1([C:4]2[C:8]([C:9]([OH:11])=O)=[C:7]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[S:25]([NH:28][C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:30])(=[O:27])=[O:26])=[CH:15][CH:14]=3)[N:6]([CH2:37][CH2:38][CH3:39])[N:5]=2)[CH2:3][CH2:2]1.C(N1C=CN=C1)([N:42]1C=CN=C1)=O.N.CCO>C1COCC1>[CH:1]1([C:4]2[C:8]([C:9]([NH2:42])=[O:11])=[C:7]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[S:25]([NH:28][C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:30])(=[O:27])=[O:26])=[CH:15][CH:14]=3)[N:6]([CH2:37][CH2:38][CH3:39])[N:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 682631,1'-CarbonyldiimidazoleHCID 10530556HCID 10530556, compound

Product 1

HCID 10506677HCID 10506677, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound obtained in example 60 (0.15 g, 0.28 mmol) in THF (10 mL) was added 1,1'-carbonyldiimidazole (0.057 g, 0.35 mmol) and the mixture was stirred at room temperature under an argon atmosphere for 3 h. Next, ammonia (32% aqueous solution, 0.33 mL) and EtOH (0.7 mL) were added and the reaction mixture was stirred at room temperature overnight and then at reflux for 1 h. The solvent was removed, the residue was taken up in CH2Cl2 and H2O was added. The aqueous phase was acidified to pH=6 and extracted with EtOAc. The combined organic extracts were dried and concentrated to a crude product. This was chromatographed on silica gel (hexane-EtOAc mixtures of increasing polarity) to afford the title compound as a white solid (40%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. temperatureat reflux for 1 h
  3. customThe solvent was removed
  4. additionH2O was added
  5. extractionextracted with EtOAc
  6. customThe combined organic extracts were dried
  7. concentrationconcentrated to a crude product
  8. customThis was chromatographed on silica gel (hexane-EtOAc mixtures of increasing polarity)

Sources & evidence

ORD record
ord-1a134bfbf8dd4616862acd85dc82fc98
Source dataset
uspto-grants-1998_10
Patent number
US05827863

Reaction notes

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