Water → HCID 53244570, compound

HRID 1805395Notes

Reaction equation

HRID 1805395 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C@:8]12[CH2:16][C@H:15]1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=[O:4].O.[OH-].[Li+]>CO>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C@@H:15]2[C@:8]3([C:7]4[C:11](=[CH:12][CH:13]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=4)[NH:10][C:9]3=[O:14])[CH2:16]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67233699HCID 67233699, compound

Product 1

HCID 53244570HCID 53244570, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1S,2R) and (1R,2S)-methyl-2-(4-fluorophenyl)-2′-oxospiro [cyclopropane-1,3′-indoline]-5′-carboxylate (80 mg) in methanol (1 mL); water (0.1 mL) was added lithium hydroxide (10 mg) at room temperature. The mixture was stirred for 14 hours at room temperature. HPLC monitored the reaction finished. The solvent was removed under reduced pressure. The residue was dissolved in 2 mL of DMF. Purification by preparative HPLC gave the title compound as white solid (30 mg). LC/MS m/e calcd. for C17H12FNO3 297, observed (M−H)+: 296. 1HNMR (400 MHz, DMSO-d6) δppm 1.99 (dd, J=9.09, 4.80 Hz, 1 H) 2.35 (dd, J=8.08, 4.80 Hz, 1 H), 3.11 (t, J=8.46 Hz, 1 H) 6.65 (d, J=1.52 Hz, 1 H) 6.94 (d, J=8.08 Hz, 1 H) 7.14 (t, J=8.84 Hz, 2 H) 7.34 (dd, J=8.34, 5.56 Hz, 2 H) 7.72 (dd, J=8.08, 1.52 Hz, 1 H) 10.97 (s, 1 H) 12.36 (br. s., 1 H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 2 mL of DMF
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-77a08549e4274cf19bdc7312a361e4b3
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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