Acetonitrile → 1-(4-Benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid hydroxyamide

HRID 2269319Notes

Reaction equation

HRID 2269319 reaction equation
C([O:4][NH:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH2:10][N:9]1[S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:7])C=C.C([O-])=O.C([NH+](CC)CC)C.C(#N)C>O>[OH:4][NH:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH2:10][N:9]1[S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:7]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10219518Triethylazanium;formateHCID 544425521-(4-Benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid allyloxy-amide

Product 1

HCID 542695771-(4-Benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid hydroxyamideYield 29.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(4-benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid allyloxy-amide (0.090 g, 0.20 mmol), triethylammonium formate (0.28 mL of a 3M solution in water, 0.83 mmol) and acetonitrile (1.1 mL) was added tetrakistriphenylphosphine palladium. After stirring for 15 min at 80° C., the mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with ether and extracted 2× into 1 M NaOH. The combined aqueous layers were washed 2× with ether, acidified with 1M HCl and extracted 3× with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated. Purification of the residue by silica gel chromatography eluting with ethyl acetate afforded 0.025 g of 1-(4-benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid hydroxyamide as a yellow solid after trituration from CH2Cl2-hexane:

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with ether
  4. extractionextracted 2× into 1 M NaOH
  5. washThe combined aqueous layers were washed 2× with ether
  6. extractionextracted 3× with ethyl acetate
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the residue by silica gel chromatography
  11. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-cbc4b75aba21408da4bcdefe91de1b02
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

Loading…