Hydrochloric Acid → 2'-Cyano-5-(2,3-dihydroxypropoxy)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845321Notes

Reaction equation

HRID 1845321 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH:18]2[CH2:22][O:21]C(C)(C)[O:19]2)[CH:13]=[C:12]([C:25]([OH:27])=[O:26])[CH:11]=1)#[N:2].Cl>C1COCC1>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH:18]([OH:19])[CH2:22][OH:21])[CH:13]=[C:12]([C:25]([OH:27])=[O:26])[CH:11]=1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 581882942'-Cyano-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4'-methylbiphenyl-3-carboxylic acid

Product 1

HCID 581883292'-Cyano-5-(2,3-dihydroxypropoxy)-4'-methylbiphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2′-cyano-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4′-methylbiphenyl-3-carboxylic acid (63 mg, 0.17 mmol) in THF (3 mL) was added 1 M of aq. HCl solution (3 mL, 3 mmol). The reaction mixture was stirred at room temperature for 4 hours, and then concentrated in vacuo. The residue was treated with water and extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4 and concentrated to afford the title compound. 1H NMR (CD3OD, 400 MHz): 7.77 (t, 1H, J=1.6 Hz), 7.67 (m, 2H), 7.58 (dd, 1H, J=8.0, 2.0 Hz), 7.51 (d, 1H, J=8.0 Hz), 7.38 (t, 1H, J=2.0 Hz), 4.19 (dd, 1H, J=9.6, 4.0 Hz), 4.10 (dd, 1H, J=9.6, 6.0 Hz), 4.02 (m, 1H), 3.72 (dd, 1H, J=11.2, 5.6 Hz), 3.67 (dd, 1H, J=11.2, 5.6 Hz), 2.45 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bb25650d6ee64d1dacbfcbe883f9951c
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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