Acetic Acid → HCID 9913530, compound

HRID 991490Notes

Reaction equation

HRID 991490 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:29][C:30]2[CH:35]=[CH:34][C:33]([O:36]C3CCCCO3)=[CH:32][CH:31]=2)[CH2:10][CH2:11][CH2:12][N:13]2[CH2:20][CH:19]3[CH2:21][CH:15]([CH2:16][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]3)[CH2:14]2)=[CH:5][CH:4]=1)#[N:2].C(O)(=O)C.O.[OH-].[Na+]>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:29][C:30]2[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=2)[CH2:10][CH2:11][CH2:12][N:13]2[CH2:14][CH:15]3[CH2:21][CH:19]([CH2:18][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:16]3)[CH2:20]2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18414054HCID 18414054, compound

Product 1

HCID 9913530HCID 9913530, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

tert-Butyl 7-{4-(4-cyanophenyl)-4-[4-(tetrahydro-2H-pyran-2-yloxy)-phenoxy]butyl}-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (from step (iv) above; 2.33 g; 4.0 mmol), was dissolved in THF (40 mL), acetic acid (20 mL) and H2O (10 mL). The mixture was stirred at 35° C. for 2 days. The mixture was made basic with 10 M NaOH (whilst cooling). Extraction with DCM, separation of the organic layer, evaporation of the solvent and chromatography on silica (CH3CN) gave 1.43 g (72%) of the title compound.

Workup

  1. extractionExtraction
  2. customwith DCM, separation of the organic layer, evaporation of the solvent and chromatography on silica (CH3CN)

Sources & evidence

ORD record
ord-b3aabe62e7524eee93c531b70da10b32
Source dataset
uspto-grants-2002_10
Patent number
US06465481B1

Reaction notes

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