Ammonium formate → N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide

HRID 2416052Notes

Reaction equation

HRID 2416052 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:32])[CH2:16][N:17](CC2C=CC=CC=2)CC2C=CC=CC=2)=[CH:11][C:10]=1[NH:33][S:34]([CH3:37])(=[O:36])=[O:35])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[NH2:17][CH2:16][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:11]=1)[OH:32]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22220247N-[2-Benzyloxy-5-(2-dibenzylamino-1-hydroxy-ethyl)-phenyl]-methanesulfonamide2×

Product 1

HCID 9837752N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred suspension of N-[2-benzyloxy-5-(2-dibenzylamino-1-hydroxy-ethyl)-phenyl]-methanesulfonamide (which was obtained in Intermediate 7)(1.03g, 2 mmol) and 10% palladium on carbon (0.4 g) in methanol (100 mL) at room temperature was added anhydrous ammonium formate (1.26 g, 20 mmol) under a nitrogen atmosphere. The resulting mixture was refluxed for 2 hours. After cooling to room temperature the catalyst was removed by filtration through a celite pad and washed with methanol. The filtrate was evaporated under reduced pressure to give the titled compound (Leclerc, G., Bizec, J. C. J. Med. Chem., 1980, 23, 738) as a pale yellowish solid; 1H NMR (300 MHz, DMSO-d6) δ 2.62 (dd, J=12.6, 8.7 Hz, 1 H), 2.75 (dd, J=12.6, 3.7 Hz, 1 H), 2.90 (s, 3 H), 4.47 (dd, J=8.7, 3.7 Hz, 1 H), 6.84 (d, J=9.1 Hz, 1 H), 6.96 (dd, J=9.1, 2.0 Hz, 1 H), 7.16 (d, J=2.1 Hz, 1 H), 8.44 (s, 1 H); MS (ES) m/z: 246.7 (MH+); HRMS Calcd. for C9H14N2O4S(M+): 246.0674. Found: 246.0672.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. customwas removed by filtration through a celite pad
  3. washwashed with methanol
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0201e910214f4b7b857ea442f62bdf4b
Source dataset
uspto-grants-2004_11
Patent number
US06821991B2

Reaction notes

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