Benzyl Chloride → HCID 86643595, compound

HRID 2381023Notes

Reaction equation

HRID 2381023 reaction equation
[CH3:1][O:2][C:3](=[O:38])[C@@H:4]([NH:27]C(OCC1C=CC=CC=1)=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]CC2C=CC=CC=2)=[C:8]([O:20][S:21](=[O:26])(=[O:25])[N:22]([CH3:24])[CH3:23])[CH:7]=1.C([Cl:46])C1C=CC=CC=1>CO.[C].[Pd]>[Cl-:46].[CH3:24][N:22]([CH3:23])[S:21]([O:20][C:8]1[CH:7]=[C:6]([CH2:5][C@H:4]([NH3+:27])[C:3]([O:2][CH3:1])=[O:38])[CH:11]=[CH:10][C:9]=1[OH:12])(=[O:26])=[O:25]

Participants

5

Reactant 2

HCID 7503Benzyl ChlorideHCID 68725215HCID 68725215, compound

Product 1

HCID 86643595HCID 86643595, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-3-dimethylsulfamoyloxy-phenyl)-propionic acid methyl ester (615 mg) was dissolved in methanol (30 ml) containing benzyl chloride (180 mg) and 5% palladium-carbon (60 mg). The mixture was stirred overnight under an atmosphere of hydrogen gas. The catalyst was removed by filtration and washed with methanol. Evaporation of the filtrate gave a gum which was crystallised by trituration with ether. (S)-2-(3-Dimethylsulfamoyloxy-4-hydroxy-phenyl)-1-methoxycarbonyl-ethyl-ammonium chloride was obtained as an off-white solid, 320 mg; NMR (500 MHz, d6 DMSO) 2.89 (3H, s), 2.97 (1H, dd J 14, 8), 3.01-3.08 (4H, m), 3.67 (3H, s), 4.19 (1H, t J 7), 6.84-6.88 (3H, m), 8.54 (ca 3H, br exch D2O), 9.58 (1H, s, exch D2O); HPLC/MS retention time 2.68 min, m/z 283 (MH+).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. customEvaporation of the filtrate
  4. customgave a gum which
  5. customwas crystallised by trituration with ether

Sources & evidence

ORD record
ord-ee6e6b1889fe4cc2b9f2cf24bdd95a10
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

Loading…