HCID 10687015, compound → HCID 10589423, compound

HRID 1451104Notes

Reaction equation

HRID 1451104 reaction equation
[OH:1][CH:2]([C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:10]([O:12][CH3:13])=[O:11])[CH2:3][N+:4]([O-])=O>C(O)C.[Pt]=O>[NH2:4][CH2:3][CH:2]([C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:10]([O:12][CH3:13])=[O:11])[OH:1]

Participants

4

Reactant 1

HCID 10687015HCID 10687015, compound

Product 1

HCID 10589423HCID 10589423, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-[1-(R,S)-hydroxy-2-nitroethyl]-4-[(methylsulfonyl)amino]benzoate (200 mg, 0.63 mmol) was dissolved in ethanol (10 mL) and hydrogenated at 50 psi in the presence of platinum oxide (Aldrich, 20 mg) for 8 h. The catalyst was removed by filtration through Celite and the filtrate concentrated to 5 mL. To the concentrate, ethyl acetate (5 mL) and hexane (10 mL) were added and the mixture cooled to 0° C. A white precipitate formed which was collected by filtration. The cake was washed with ethyl acetate:hexane (1:1) and dried to give 100 mg (55%) of methyl 3-[2-amino-1-(R,S)-hydroxyethyl]-4-[(methylsulfonyl)amino]benzoate as a white powder, mp 172°-173° C. (dec).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate concentrated to 5 mL
  3. additionTo the concentrate, ethyl acetate (5 mL) and hexane (10 mL) were added
  4. customA white precipitate formed which
  5. filtrationwas collected by filtration
  6. washThe cake was washed with ethyl acetate:hexane (1:1)
  7. customdried

Sources & evidence

ORD record
ord-a84e831e99d64cdda50b5b9f505371d9
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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