Water → HCID 58305288, compound

HRID 1805339Notes

Reaction equation

HRID 1805339 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@@:12]3([CH2:20][C@@H:19]3[C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[C:11]2=[O:28])[CH:5]=1.COC(=O)C1C=CC=C(N2C3C(=CC=CC=3)[C@]3(C[C@H]3C3C=CC(Cl)=CC=3)C2=O)C=1.O.[OH-].[Li+]>CO>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C@H:19]2[C@@:12]3([C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:10]([C:6]4[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=4)[C:3]([OH:29])=[O:2])[C:11]3=[O:28])[CH2:20]2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 58305377HCID 58305377, compoundHCID 58305406HCID 58305406, compound

Product 1

HCID 58305288HCID 58305288, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl-3-((1S,2R)-2-(4-chlorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)benzoate and methyl-3-((1R,2S)-2-(4-chlorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)benzoate (50 mg) in 1 mL of methanol was added 0.1 mL of water, followed by lithium hydroxide (10 mg), 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 a white powder. (11 mg) LC/MS m/e calcd. for C23H16ClNO3 389, observed (M+H)+: 390.1. 1H NMR (400 MHz, DMSO-d6) δppm 2.14 (dd, J=9.09, 5.05 Hz, 1 H) 2.41 (dd, J=8.08, 5.05 Hz, 1 H) 3.25 (t, J=8.59 Hz, 1 H) 6.19 (d, J=7.33 Hz, 1 H) 6.77-6.86 (m, 2 H) 7.12 (t, J=7.71 Hz, 1 H) 7.36-7.46 (m, 4 H) 7.72 (t, J=7.83 Hz, 1 H) 7.76-7.85 (m, 1 H) 8.01-8.09 (m, 2 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-932fd61820194893aae501ec3ca3fc74
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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