Lithium hydroxide, monohydrate → HCID 11999003, compound

HRID 2102748Notes

Reaction equation

HRID 2102748 reaction equation
C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]3([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=4)[C:27]4[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:29])[CH2:14]2)=[O:12])[CH:5]=1.O.[OH-].[Li+]>O1CCCC1>[Cl:28][C:24]1[CH:23]=[C:22]2[C:27]([C:19]([CH:15]3[CH2:16][CH2:17][CH2:18][N:13]([C:11]([NH:10][C:6]4[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=4)[C:3]([OH:38])=[O:2])=[O:12])[CH2:14]3)([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=3)[C:20](=[O:29])[NH:21]2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11999002HCID 11999002, compound

Product 1

HCID 11999003HCID 11999003, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of rac-3-({3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carbonyl}-amino)-benzoic acid methyl ester (50 mg, 0.090 mmol) (from Example 68 supra) in tetrahydro furan (2 mL) was added the suspension of lithium hydroxide monohydrate (38 mg, 0.9 mmol) (Aldrich). The mixture was stirred at room temperature for 2 days. The solvent was removed and the residue was partitioned between ethyl acetate and water. The aqueous layer was acidified to pH<5 with dilute HCl, then extracted with ethyl acetate several times. The combined organic layer was washed with water, brine, dried over MgSO4 and concentrated. The rsidue was triturated with Dichloromethane-Hexane to give rac-3-({3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carbonyl}-amino)-benzoic acid as a white solid. (Yield 40 mg, 81.6%).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionextracted with ethyl acetate several times
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe rsidue was triturated with Dichloromethane-Hexane

Sources & evidence

ORD record
ord-e5777d8216144ad189a2eab48e4e2814
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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