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Water → 3-Naphthalen-2-ylmethyl-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylic acid (4-methoxyphenyl)amide

HRID 1691657
Notes
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Reaction equation

HRID 1691657 reaction equation
C(OC([N:8]1[CH2:29][CH2:28][C:11]2([O:15][C:14](=[O:16])[N:13]([CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=3)[CH2:12]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[CH3:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([N:45]=[C:46]=[O:47])=[CH:41][CH:40]=1.O>C(Cl)Cl.CCOC(C)=O>[CH3:37][O:38][C:39]1[CH:40]=[CH:41][C:42]([NH:45][C:46]([N:8]2[CH2:29][CH2:28][C:11]3([O:15][C:14](=[O:16])[N:13]([CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[CH:19]=4)[CH2:12]3)[CH2:10][CH2:9]2)=[O:47])=[CH:43][CH:44]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 794431-Isocyanato-4-methoxybenzeneHCID 104084473-Naphthalen-2-ylmethyl-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylic acid tert-butyl ester

Product 1

HCID 119922213-Naphthalen-2-ylmethyl-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylic acid (4-methoxyphenyl)amide

Reagents, catalysts & solvents

2
HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound A7 (0.50 g, 1.26 mmol) was dissolved in DCM (3 mL) and combined with trifluoroacetic acid (3 mL). The reaction mixture was stirred for 5 min at RT and the solvent was then removed under a vacuum. The residue was combined repeatedly with toluene and the solvent was then removed again. The residue was then combined with sat. aq. NaHCO3 solution and repeatedly extracted with EtOAc. The combined organic phases were dried over Na2SO4 and the solvent was removed under a vacuum. The residue was redissolved in anhydrous THF (5 mL) and combined with a little triethylamine. The reaction mixture was combined with 4-methoxyphenyl isocyanate (202 mg, 1.35 mmol), stirred for 18 h at RT and combined with water and EtOAc. The organic phase was separated off and the aqueous phase repeatedly extracted with EtOAc. The combined organic phases were dried over Na2SO4 and the solvent was removed under a vacuum. The residue was purified by column chromatography (SiO2, heptane/EtOAc 2:1). After crystallisation from heptane and DCM, 237 mg (42% of theoretical) of the desired product 3-naphthalen-2-ylmethyl-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylic acid (4-methoxyphenyl)amide (52) were obtained.

Workup

  1. customthe solvent was then removed under a vacuum
  2. customthe solvent was then removed again
  3. extractionrepeatedly extracted with EtOAc
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customthe solvent was removed under a vacuum
  6. dissolutionThe residue was redissolved in anhydrous THF (5 mL)
  7. stirringstirred for 18 h at RT
  8. customThe organic phase was separated off
  9. extractionthe aqueous phase repeatedly extracted with EtOAc
  10. dry with materialThe combined organic phases were dried over Na2SO4
  11. customthe solvent was removed under a vacuum
  12. customThe residue was purified by column chromatography (SiO2, heptane/EtOAc 2:1)
  13. customAfter crystallisation from heptane and DCM, 237 mg (42% of theoretical) of the desired product 3-naphthalen-2-ylmethyl-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylic acid (4-methoxyphenyl)amide (52)
  14. customwere obtained

Sources & evidence

ORD record
ord-8a16e0afd3ea4aa2834c0fa3bf02bee1
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153795B2

Reaction notes

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