p-Toluenesulfonic acid → 4-Hydroxymethyl-2'-(methoxycarbonyl)amino-1,1'-biphenyl

HRID 1647325Notes

Reaction equation

HRID 1647325 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH:21][C:22]([O:24][CH3:25])=[O:23])=[CH:11][CH:10]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[OH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH:21][C:22]([O:24][CH3:25])=[O:23])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 218366964-(Tetrahydropyranyloxy)methyl-2'-(methoxycarbonyl)amino-1,1'-biphenyl

Product 1

HCID 218367054-Hydroxymethyl-2'-(methoxycarbonyl)amino-1,1'-biphenylYield 72.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude 4-(tetrahydropyranyloxy)methyl-2'-(methoxycarbonyl)amino-1,1'-biphenyl (250 mg) dissolved in 4 mL of methanol was treated with 1 mL of 10% methanolic p-toluenesulfonic acid. The reaction mixture was stirred at room temperature for 1 hour. The s reaction mixture was made basic by the addition of saturated aqueous sodium bicarbonate, then diluted with ethyl acetate. The organic layer was washed with water (2×), dried over magnesium sulfate and evaporated under vacuum. The residue was purified by preparative thin layer chromatography on silica gel, eluting with methylene chloride-methanol (100:3) to give 137 mg of the product. 1H NMR (200 MHz, CDCl3): δ3.51 (s, 3H), 4.75 (s, 2H), 6.62 (br s, 1H), 7.14 (dd, 2H), 7.34 (dd, 1H), 7.4 (dd, 4H). FAB-MS (Li+ spike): calculated for C15H15NO3 (257); found 264 (M+Li).

Workup

  1. customThe s reaction mixture
  2. washThe organic layer was washed with water (2×)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum
  5. customThe residue was purified by preparative thin layer chromatography on silica gel
  6. washeluting with methylene chloride-methanol (100:3)

Sources & evidence

ORD record
ord-a1276876495f451a89ab72a4b1e74774
Source dataset
uspto-grants-1995_07
Patent number
US05430144

Reaction notes

Loading…