Methanol → 4'-Methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid

HRID 1845190Notes

Reaction equation

HRID 1845190 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:11]=[C:10]([C:21]([O:23]CC)=[O:22])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+].CO>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:11]=[C:10]([C:21]([OH:23])=[O:22])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 58188240Ethyl 4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate

Product 1

HCID 581879754'-Methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate (3.94 g, 11.7 mmol), lithium hydroxide (0.65 g, 27.1 mmol), MeOH (250 mL), and water (40 mL) was stirred at rt for 20 hr. LC-MS indicated completion of the reaction. The solvent was removed in vacuo and the residue was treated with water and acidified with 1N aq. HCl to pH=2-3. The aqueous phase was extracted with EtOAc (3×100 mL). The combined organic layers were washed with water, brine, dried and concentrated to yield the product as a white solid. LC-MS: 310.4 [M+1]+; 1H NMR (400 MHz, DMSO-d6): 13.29 (s, 1H), 8.21 (t, 1H, J=1.6 Hz), 7.99 (t, 1H, J=1.6 Hz), 7.98 (t, 1H, J=1.5 Hz), 7.64 (d, 2H, J=8.2 Hz), 7.31 (d, 2H, J=7.9 Hz), 3.50 (t, 2H, J=6.7 Hz), 3.43 (t, 2H, J=6.5 Hz), 2.36 (s, 3H), 1.98-1.78 (m, 4H).

Workup

  1. customcompletion of the reaction
  2. customThe solvent was removed in vacuo
  3. additionthe residue was treated with water
  4. extractionThe aqueous phase was extracted with EtOAc (3×100 mL)
  5. washThe combined organic layers were washed with water, brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f2b7bc00d02e43f9ab7102d0d660dd2d
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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