Water → (1-[4-(3-Chloro-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

HRID 1037392Notes

Reaction equation

HRID 1037392 reaction equation
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19](=[O:37])[C:20]4[C:25]([O:26][C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:24]3[NH:34][N:35]=[CH:36][C:23]3=[CH:22][CH:21]=4)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:39][O-].[Na+].CCOC(C)=O.O>CCO.C1CCCCC1>[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19](=[O:37])[C:20]4[C:25]([O:26][C:27]=3[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[C:24]3[NH:34][N:35]=[C:36]([Cl:39])[C:23]3=[CH:22][CH:21]=4)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 23665760Sodium Hypochlorite2×HCID 67067899{1-[4-(6-Oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester2×

Product 1

HCID 178452581(1-[4-(3-Chloro-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl esterYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8078CyclohexaneSolvent

Procedure

To a stirred solution of {1-[4-(6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (5 mg, 0.01 mmol) in EtOH (1 mL), was added sodium hypochlorite (10% aqueous solution, 0.4 mL) at RT. After 2 h, EtOAc and water were added. The resulting biphasic mixture was separated. The aqueous phase was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The reaction was repeated with {1-[4-(6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (20 mg, 0.039 mmol) and aqueous sodium hypochlorite (2 mL) in EtOH (3 mL) with initial cooling in a cold water bath. After workup, the resultant residues were combined and subjected to flash chromatography (SiO2, gradient 20 to 40% EtOAc in cyclohexane) to afford the title compound (16 mg, 60%) as a white solid. LCMS (Method H): RT=4.39 min, [M+H]+=542/544.

Workup

  1. customThe resulting biphasic mixture was separated
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. temperaturewith initial cooling in a cold water bath

Sources & evidence

ORD record
ord-0f0335fc80f141cf946c92c801d2468e
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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