Hydrochloric Acid → HCID 68537017, compound

HRID 1441670Notes

Reaction equation

HRID 1441670 reaction equation
[O:1]1CCC[CH2:3][CH:2]1[O:7][CH2:8][CH2:9][N:10]1[C:23]2[C:18](=[CH:19][C:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:22]=2)[C:12]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:11]1=[O:31].Cl.C(N(CC)CC)C.C(OC(=O)C)(=O)C>CO.ClCCl>[CH3:3][C:2]([O:7][CH2:8][CH2:9][N:10]1[C:23]2[C:18](=[CH:19][C:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:22]=2)[C:12]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:11]1=[O:31])=[O:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68539560HCID 68539560, compound

Product 1

HCID 68537017HCID 68537017, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-(tetrahydropyran-2-yl-oxy-ethyl)-5-tert-butoxycarbonyl-spiro[indoline-3,4′-piperidin]-2-one (0.021 g, 0.05 mmol) was dissolved in methanol (2 mL). To the reaction mixture was then added at room temperature aqueous 1.0N HCl (80 μL) and the reaction mixture was stirred for 30 minutes. The reaction mixture was then partitioned with aqueous Na2CO3 and ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a solid. The solid was then dissolved in dry dichloromethane (2 mL). To the reaction mixture was then added at 0° C. triethylamine (0.12 g, 0.12 mmol) and acetic anhydride (0.02 g, 0.2 mmol) under nitrogen atmosphere and the reaction mixture was stirred at 0° C. for 30 minutes and 18 hrs at room temperature. The reaction mixture was then partitioned with aqueous Na2CO3 and dichloromethane. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield the title compound as a gum.

Workup

  1. customThe reaction mixture was then partitioned with aqueous Na2CO3 and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a solid
  7. stirringthe reaction mixture was stirred at 0° C. for 30 minutes and 18 hrs at room temperature
  8. customThe reaction mixture was then partitioned with aqueous Na2CO3 and dichloromethane
  9. washThe organic layer was washed with brine
  10. dry with materialdried with Na2SO4
  11. filtrationfiltered
  12. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-0a4db2bcbc22479094462813562f6ad8
Source dataset
uspto-grants-2010_02
Patent number
US07655670B2

Reaction notes

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