HCID 15376565, compound → HCID 15376564, compound

HRID 2187500Notes

Reaction equation

HRID 2187500 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:18]=[C:17]([CH2:19][C:20]#[N:21])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.Cl.O.[Pt]=O>[NH2:21][CH2:20][CH2:19][C:17]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])[CH:18]=1

Participants

5

Reactant 1

HCID 15376565HCID 15376565, compound

Product 1

HCID 15376564HCID 15376564, compound

Reagents, catalysts & solvents 3

HCID 86587499Platinum oxide monohydrateCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

After 0.5 g of platinum oxide hydrate had been added to a solution of 2.5 g (8.05 mmol) of methyl 2-(tert-butylaminosulfonyl)-4-cyanomethylbenzoate in 200 ml of methanol and 4 ml of concentrated HCl, the mixture was hydrogenated for 10 hours at room temperature and under a hydrogen pressure of 20 bar. For working-up, the catalyst was removed by filtration and the filtrate was concentrated. After the residue had been taken up in ethyl acetate, the solution was washed four times with 2 N HCl. The combined acidic aqueous phases are brought to pH 10-11 with concentrated ammonia and extracted three times with ethyl acetate. The organic extracts were dried over Na2SO4 and concentrated in vacuo. This gave 1.9 g (75%) of methyl 4-(2-aminoethyl)-2-tert-butylaminosulfonylbenzoate as an oil.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. washthe solution was washed four times with 2 N HCl
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe organic extracts were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f0be5766dc034474a68c9b98369bc648
Source dataset
uspto-grants-2002_06
Patent number
US06410483B1

Reaction notes

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