Sodium Hydroxide → 4-(3-{4-[(tert-Butoxycarbonyl-cyclopropyl-amino)-methyl]-piperidin-1-yl}-3-oxo-propyl)-3-methyl-benzoic Acid

HRID 220935Notes

Reaction equation

HRID 220935 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:36])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:25]3[CH2:27][CH2:26]3)[CH2:19][CH2:18]2)=[O:16])=[C:9]([CH3:35])[CH:8]=1.[OH-].[Na+]>C1COCC1.O>[C:31]([O:30][C:28]([N:24]([CH2:23][CH:20]1[CH2:21][CH2:22][N:17]([C:15](=[O:16])[CH2:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:36])=[O:5])=[CH:8][C:9]=2[CH3:35])[CH2:18][CH2:19]1)[CH:25]1[CH2:27][CH2:26]1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 575553004-(3-{4-[(tert-Butoxycarbonyl-cyclopropyl-amino)-methyl]-piperidin-1-yl}-3-oxo-propyl)-3-methyl-benzoic Acid Methyl Ester

Product 1

HCID 575553264-(3-{4-[(tert-Butoxycarbonyl-cyclopropyl-amino)-methyl]-piperidin-1-yl}-3-oxo-propyl)-3-methyl-benzoic AcidYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (142 mg, 3.4 mmol) was added to a solution of 4-(3-{4-[(tert-butoxycarbonyl-cyclopropyl-amino)-methyl]-piperidin-1-yl}-3-oxo-propyl)-3-methyl-benzoic acid methyl ester from Example E86.1 (1.41 g, 3.1 mmol) in THF (20 ml) and water (2 ml). The mixture was stirred for 16 h at room temperature then 1M NaOH solution (5 ml) was added. The mixture was heated at 60° C. for 3 h then concentrated in vacuo. The residue was dissolved in EtOAc, washed with 1M HCl then brine, dried and concentrated in vacuo to yield the title compound (1.25 g, 91%).

Workup

  1. temperatureThe mixture was heated at 60° C. for 3 h
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 1M HCl
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92a456aaf7f340a0b90185cb13c058ff
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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