Acetoacetic Acid → HCID 86625997, compound

HRID 1992345Notes

Reaction equation

HRID 1992345 reaction equation
[ClH:1].CC(CC(O)=O)=O.C(OC(=O)[NH:15][CH2:16][CH2:17][N:18]1[CH2:25][CH:24]2[O:26][CH:20]([CH2:21][N:22]([CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=3)[CH2:23]2)[CH2:19]1)(C)(C)C>O1CCOCC1>[ClH:1].[ClH:1].[ClH:1].[NH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH:20]2[O:26][CH:24]([CH2:23][N:22]([CH2:27][CH2:28][O:29][C:30]3[CH:31]=[CH:32][C:33]([C:36]#[N:37])=[CH:34][CH:35]=3)[CH2:21]2)[CH2:25]1

Participants

5

Reactant 3

HCID 96Acetoacetic AcidHCID 313Hydrochloric Acid2×HCID 9953719HCID 9953719, compound

Product 1

HCID 86625997HCID 86625997, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Hydrochloric acid (140 mmol, 35 mL of a 4 M solution in dioxane) was added to an ice-cooled slurry of the diacetate salt of (2-{7-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl}ethyl)carbamic acid tert-butyl ester (10.75 g, 20 mmol; see step (i) above) in dioxane (50 mL). The reaction mixture was stirred at RT overnight. Another 65 mL (260 mmol) of 4 M HCl solution was added, after which the reaction mixture was stirred for three hours and then evaporated. The residue was dissolved in water and washed with diethyl ether. Freeze-drying of the aqueous phase gave 8.3 g (97%) the title compound as a white solid.

Workup

  1. stirringafter which the reaction mixture was stirred for three hours
  2. customevaporated
  3. dissolutionThe residue was dissolved in water
  4. washwashed with diethyl ether
  5. customFreeze-drying of the aqueous phase

Sources & evidence

ORD record
ord-25cc9f6b51ed45c0855a3d46e9ef32f7
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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