Hydrochloric Acid → HCID 57695593, compound

HRID 2079857Notes

Reaction equation

HRID 2079857 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([C:33]2[CH:38]=[C:37]([CH:39]([CH3:41])[CH3:40])[CH:36]=[CH:35][C:34]=2[O:42][CH3:43])[C:14]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:10])C1C=CC=CC=1.[Li+].[OH-].Cl>C1COCC1.O>[CH2:18]([O:17][C:16]1[CH:15]=[C:14]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:13]([C:33]2[CH:38]=[C:37]([CH:39]([CH3:41])[CH3:40])[CH:36]=[CH:35][C:34]=2[O:42][CH3:43])=[CH:12][C:11]=1[C:9]([OH:10])=[O:8])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67102424HCID 67102424, compound

Product 1

HCID 57695593HCID 57695593, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

4,6-Bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid benzyl ester (573 mg, 1 mmol) was dissolved in a mixture of THF (5 ml) and water (5 ml). LiOH (72 mg, 3 mmol) was added, and the resulting mixture was stirred at 90° C. overnight. After the reaction was complete, the reaction mixture was cooled to r.t., acidified with 1M HCl to pH=1. After extraction with Et2O (25 ml×3), the combined organics were washed with water and brine and dried over Na2SO4. After filtration and concentration, 4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid was obtained as a white solid (463 mg, 96%). M.p.: 181-182° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.56-7.53 (m, 2H), 7.43-7.39 (m, 2H), 7.36-7.28 (m, 7H), 7.16 (dd, J=8.4, 2.0 Hz, 1H), 7.03 (d, J=2.0 Hz, 1H), 6.98-6.93 (m, 2H), 5.27 (s, 2H), 5.17 (s, 2H), 3.65 (s, 3H), 2.84 (hept, J=6.8 Hz, 1H), 1.17 (d, J=6.8 Hz, 6H); LCMS: 483 [M+1].

Workup

  1. temperaturethe reaction mixture was cooled to r.t.
  2. extractionAfter extraction with Et2O (25 ml×3)
  3. washthe combined organics were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-488f5caa8bf44b668e9d769541a6c9f7
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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