Water → HCID 78324476, compound

HRID 2201948Notes

Reaction equation

HRID 2201948 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][CH2:23][C:24]([O:26]CC)=[O:25])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.O.[Li+].[OH-]>C1COCC1.CO>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 78324475HCID 78324475, compound

Product 1

HCID 78324476HCID 78324476, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (R)-Ethyl 2-((4′-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)methoxy)acetate (125.6 mg, 0.329 mmol) in THF (0.5 mL), MeOH (0.5 mL), and H2O (1 mL) was added LiOH (23.65 mg, 0.988 mmol). The reaction was heated briefly to ˜50° C. and concentrated. The resulting aqueous mixture was acidified (HCl, 3 eq) and purified by HPLC to give the title compound. LCMS m/z=354.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37 (t, J=5.94 Hz, 3H), 1.53-1.70 (m, 1H), 1.86-2.13 (m, 2H), 2.16-2.28 (m, 1H), 2.91-3.13 (m, 2H), 3.16-3.27 (m, 2H), 3.51-3.71 (m, 3H), 4.09 (s, 2H), 4.58 (s, 2H), 7.37-7.47 (m, 4H), 7.61-7.70 (m, 4H), 9.26-9.84 (m, 1H), 12.68 (bs, 1H).

Workup

  1. concentrationconcentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-6b3594b2165a44edb51b9d9fab8e20f9
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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