Lithium Hydroxide → HCID 53244571, compound

HRID 1805398Notes

Reaction equation

HRID 1805398 reaction equation
C(C1C=CC([C@@H]2[C@]3(C4C(=CC=C(C(O)=O)C=4)NC3=O)C2)=CC=1)#N.C[O:25][C:26]([C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32](=[O:37])[C@@:31]12[CH2:39][C@@H:38]1[C:40]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=1)=[O:27].[OH-].[Li+]>CO.O>[F:46][C:43]1[CH:42]=[CH:41][C:40]([C@H:38]2[C@@:31]3([C:30]4[C:34](=[CH:35][CH:36]=[C:28]([C:26]([OH:27])=[O:25])[CH:29]=4)[NH:33][C:32]3=[O:37])[CH2:39]2)=[CH:45][CH:44]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 53244569HCID 53244569, compoundHCID 67233146HCID 67233146, compound

Product 1

HCID 53244571HCID 53244571, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution (1R,2S) and (1S,2R)-methyl-2-(4-fluorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-5′-carboxylate (80 mg) (prepared as in Example 139) in methanol (1 mL) and 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. Purification by preparative HPLC gave the title compound as white solid (30 mg). LC/MS m/e calcd. for C17H12FNO3: 297, observed (M+H)+: 298.2 LC/MS m/e calcd for C17H12FNO3297.08, observed (M−H)+: 296.1; 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. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-54e371b4f9074647b2bdb46bdc1058b7
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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