Water → HCID 53244689, compound

HRID 1805305Notes

Reaction equation

HRID 1805305 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19]OC(=O)C4C=CC=CC=4)[C:11]3=[O:29])[CH2:9]2)=[CH:4][CH:3]=1.[OH2:30].[OH-:31].[Li+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[C@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19][C:3]4[CH:4]=[C:5]([CH:6]=[CH:7][CH:2]=4)[C:8]([OH:31])=[O:30])[C:11]3=[O:29])[CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86654392((2-(4-Chlorophenyl)-2'-oxospiro[cyclo-propane-1,3'-indoline]-1'-yl)methyl)benzoate

Product 1

HCID 53244689HCID 53244689, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1R,2S) and (1S,2R)-methyl-3-(((2-(4-chlorophenyl)-2′-oxospiro[cyclo-propane-1,3′-indoline]-1′-yl)methyl)benzoate (48 mg) was dissolved in 1 mL of methanol; then 0.1 mL of water was added followed by lithium hydroxide (10 mg). The mixture was stirred for 14 hours at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in 2 mL of DMF and purified by preparative HPLC to give the title compound as white powder (10 mg). LC/MS m/e calcd. for C24H18ClNO3: 403, observed (M+H)+: 404.1 1H NMR (400 MHz, DMSO-d6) δppm 2.12 (dd, J=9.09, 4.80 Hz, 1H) 2.40 (dd, J=7.96, 4.93 Hz, 1H) 3.19-3.24 (m, 1 H) 5.10 (s, 2H) 6.17 (d, J=7.33 Hz, 1H) 6.72 (t, J=7.58 Hz, 1H) 6.95 (d, J=7.83 Hz, 1H) 7.08 (t, J=7.83 Hz, 1H) 7.30-7.41 (m, 4H) 7.50 (t, J=7.71 Hz, 1H) 7.60 (d, J=7.58 Hz, 1H) 7.82-7.89 (m, 2 H) 13.04 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-f201501db305477fbfe89ec114d4e6ee
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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