Sulfamic Acid → 2-Methoxy-3'-carboethoxy-[1,1'-biphenyl]-6-carboxylic acid

HRID 275171Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]=[O:10])[C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=1.S(=O)(=O)([OH:24])N.Cl([O-])=O.[Na+].CCOC(C)=O>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:24])=[O:10])[C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Aldehyde 4a (0.512 g., 1.80 mmol, 1 equiv.) is dissolved in 17 mL of THF and 13 mL of H2O. The solution is cooled to 0° C. Sulfamic acid (0.525 g., 5.41 mmol, 3 equiv. ) is then added, followed by a solution of sodium chlorite (80% tech., 0.612 g., 5.41 mmol, 3 equiv. ) in 4 mL of H2O. The mixture is stirred for 15 min. at 0° C., and then poured into EtOAc and water. The aqueous layer is extracted thrice with EtOAc, and the combined organic-phase is washed with brine. The organic phase is dried (MgSO4) and then concentrated in vacuo to afford 2-methoxy-3'-carboethoxy-[1,1'-biphenyl]-6-carboxylic acid (5a) as a pale yellow oil (0.583 g., 1.80 mmol, 100%): 1H NMR (300 MHz, CDCl3) δ 10.17 (br, 1H, C2H), 8.02 (ddd, J=2, 2, 8 Hz, 1H, ArH), 7.94 (s, 1H, ArH), 7.56 (d, J=8 Hz, 1H, ArH), 7.41 (m, 3H, ArH), 7.15 (d, J=8 Hz, 1H, ArH), 4.19 (q, J=7 Hz, 2H, CO2CH2), 3.,73 (s, 3H, OCH3), 1.39 (t, J=7 Hz, 3H, CH2CH3).

Workup

extractionThe aqueous layer is extracted thrice with EtOAc
washthe combined organic-phase is washed with brine
dry with materialThe organic phase is dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ccb2c8474b4f499b9b3a00086932e0c1
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05391817

Reaction notes

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