Methanol → 5-(3-Hydroxyazetidine-1-carbonyl)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845183Notes

Reaction equation

HRID 1845183 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([C:8]2[CH:9]=[C:10]([C:21]([O:23]CC)=[O:22])[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[CH:13]=2)=[O:7])[CH2:3]1.[OH-].[Li+].CO>O>[OH:1][CH:2]1[CH2:3][N:4]([C:6]([C:8]2[CH:9]=[C:10]([C:21]([OH:23])=[O:22])[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)[CH:13]=2)=[O:7])[CH2:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 58187978Ethyl 5-(3-hydroxyazetidine-1-carbonyl)-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 581883575-(3-Hydroxyazetidine-1-carbonyl)-4'-methylbiphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 5-(3-hydroxyazetidine-1-carbonyl)-4′-methylbiphenyl-3-carboxylate (2.0 g, 5.9 mmol), lithium hydroxide (0.56 g, 24 mmol), methanol (100 mL), and water (10 mL) was stirred at rt for 4 h. 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 and extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to yield a white solid. LC-MS: 312.4 [M+1]+; 1H NMR (400 MHz, DMSO-d6): 13.30 (bs, 1H), 8.26 (s, 1H), 8.09 (s, 1H), 8.03 (s, 1H), 7.64 (d, 2H, J=8.0 Hz), 7.32 (d, 2H, J=8.0 Hz), 5.79 (bs, 1H), 4.52 (s, 2H), 4.30 (bs, 1H), 4.10 (bs, 1H), 3.84 (d, 1H, J=9.6 Hz), 2.37 (s, 3H).

Workup

  1. customcompletion of the reaction
  2. customThe solvent was removed in vacuo
  3. additionthe residue was treated with water
  4. extractionextracted with EtOAc (50 mL×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto yield a white solid

Sources & evidence

ORD record
ord-38742cc06e9e4841929cec557fc4a848
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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