Tetrahydrofuran → HCID 178482215, compound

HRID 1497533Notes

Reaction equation

HRID 1497533 reaction equation
NC1C([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)=C(O)C=CC=1.[C:16]([O:20][C:21]([NH:23][C:24](=[N:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[NH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([O-:32])=[O:31])=[CH:28][CH:27]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17].O1CCCC1.[N:48]1(CO)[C:52]2C=CC=CC=2N=N1>C(O)C>[C:39]([O:38][C:36]([NH:35][C:24](=[N:23][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[NH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([O:32][C:13]2[CH:14]=[CH:9][C:10]([NH:48][CH3:52])=[C:11]([Cl:15])[CH:12]=2)=[O:31])=[CH:28][CH:27]=1)=[O:37])([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2241691H-Benzotriazole-1-methanolHCID 178454297HCID 178454297, compound

Product 1

HCID 178482215HCID 178482215, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4 amino-3-chlorophenylphenol 4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoate (600 mg) in ethanol (6.00 mL)-tetrahydrofuran (6.00 mL) was added 1H-1,2,3-benzotriazole-1-ylmethanol (195 mg), followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and then to the residue were added N,N-dimethylformamide (6.00 mL) and tetrahydrofuran (6.00 mL). Sodium borohydride (89.9 mg) was added thereto under ice-cooling, followed by stirring at room temperature for 3 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 3-chloro-4-(methylamino)phenyl 4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoate (362 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue were added N,N-dimethylformamide (6.00 mL) and tetrahydrofuran (6.00 mL)
  3. additionSodium borohydride (89.9 mg) was added
  4. temperatureunder ice-cooling
  5. stirringby stirring at room temperature for 3 hours
  6. additionTo the reaction mixture was added water
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-826ef6cc2437490dbe197611a5b1edc8
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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