Lithium Hydroxide → HCID 58305364, compound

HRID 1805397Notes

Reaction equation

HRID 1805397 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1)[C:9](=[O:22])[C@@:8]12[CH2:24][C@@H:23]1[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=[O:4].[OH-].[Li+]>CO.C1COCC1.O>[F:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][N:10]1[C:11]2[C:7](=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:13][CH:12]=2)[C@@:8]2([CH2:24][C@@H:23]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:9]1=[O:22]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 67233992HCID 67233992, compound

Product 1

HCID 58305364HCID 58305364, compoundYield 20.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (1R,2S) and (1S,2R)-methyl-1′-(3-fluorobenzyl)-2-(4-fluorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-5′-carboxylate (50 mg) in methanol (5 mL), THF (5 mL) and water (1 mL) was added lithium hydroxide (50 mg) at room temperature. The mixture was heated to 60° C. and stirred at 60° C. for 3 hours. HPLC monitored the reaction finished. The solvent was removed under reduced pressure. Purification by preparative HPLC gave the title compound as white powder (10 mg). LC/MS m/e calcd. for C24H17F2lNO3: 405, observed (M+H)+: 406.2 1H NMR (400 MHz, MeOD) δppm 7.83 (dd, J=8.34, 1.52 Hz, 1 H) 7.24-7.38 (m, 5 H) 7.15 (d, J=2.02 Hz, 1 H) 7.18 (d, J=7.83 Hz, 2 H) 7.06 (t, J=8.72 Hz, 2 H) 6.99 (d, J=8.08 Hz, 1 H) 6.75 (d, J=1.52 Hz, 1 H) 5.17 (s, 2 H) 2.24-2.35 (m, 2 H); MS calcd. C24H17F2NO3 406, obsd. (ESI+) [(M+H)+] 406.4.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-3da53caca384423ba0d3cad376e3827d
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

Loading…