Lithium hydroxide, monohydrate → HCID 11999357, compound

HRID 2102767Notes

Reaction equation

HRID 2102767 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][CH2:17][CH:16]([C:20]3([CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=4)[C:28]4[C:23](=[CH:24][C:25]([Cl:29])=[CH:26][CH:27]=4)[NH:22][C:21]3=[O:30])[CH2:15]2)=[O:13])=[CH:7][N:6]=1)=[O:4].O.[OH-].[Li+]>O1CCCC1.O>[Cl:29][C:25]1[CH:24]=[C:23]2[C:28]([C:20]([CH:16]3[CH2:17][CH2:18][CH2:19][N:14]([C:12]([NH:11][C:8]4[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=4)=[O:13])[CH2:15]3)([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=3)[C:21](=[O:30])[NH:22]2)=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11999237HCID 11999237, compound

Product 1

HCID 11999357HCID 11999357, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of rac-5-({3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carbonyl}-amino)-pyridine-2-carboxylic acid methyl ester (67 mg, 0.12 mmol) (from Example 83 d supra) in tetrahydrofuran (2 mL) was added the suspension of lithium hydroxide monohydrate (51 mg, 1.2 mmol) (Aldrich) in water (2 mL). The mixture was stirred at room temperature for overnight. 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 to give rac-5-({3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carbonyl}-amino)-pyridine-2-carboxylic acid as a white solid. (Yield 45 mg, 69.2%).

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

Sources & evidence

ORD record
ord-b59477cd98f548efa36de18d9138230a
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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