Water → HCID 53244689, Verbindung

HRID 1805305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805305
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 53244689HCID 53244689, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f201501db305477fbfe89ec114d4e6ee
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354443B2

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