Sodium Carbonate → HCID 42605612, compound

HRID 1096435

Reaction equation

HRID 1096435 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[OH:7][C:8]([CH3:41])([CH3:40])[CH2:9][C@@:10]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:15][C:14](=[O:16])[N:13]([C@H:17]([C:19]2[CH:24]=[CH:23][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:21][CH:20]=2)[CH3:18])[CH2:12][CH2:11]1.Br[C:43]1[CH:44]=[CH:45][C:46](=[O:53])[N:47]([CH2:49][CH:50]2[CH2:52][CH2:51]2)[CH:48]=1>CN(C)C=O>[CH:50]1([CH2:49][N:47]2[C:46](=[O:53])[CH:45]=[CH:44][C:43]([C:22]3[CH:21]=[CH:20][C:19]([C@@H:17]([N:13]4[CH2:12][CH2:11][C@:10]([CH2:9][C:8]([OH:7])([CH3:40])[CH3:41])([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[O:15][C:14]4=[O:16])[CH3:18])=[CH:24][CH:23]=3)=[CH:48]2)[CH2:52][CH2:51]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-oneHCID 596357015-Bromo-1-(cyclopropylmethyl)-1,2-dihydropyridin-2-one

Product 1

HCID 42605612HCID 42605612, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2 M aqueous Na2CO3 solution (0.84 mL) was added to a solution of (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-[(S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl]-1,3-oxazinan-2-one (0.40 g) and 5-bromo-1-cyclopropylmethyl-1H-pyridin-2-one (0.24 g) in dimethyl-formamide (4 mL). The resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (34 mg) was added. The mixture was heated to 100° C. and stirred at this temperature for 4 h. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel (dichloromethane/methanol 99:1->95:5) to afford the title compound that was crystallized with little ethyl acetate. Yield: 0.19 g (46% of theory); Mass spectrum (ESI+): m/z=501 [M+H]+.

Workup

  1. customThe resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (34 mg)
  2. additionwas added
  3. temperatureAfter cooling to ambient temperature
  4. additionwater was added
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel (dichloromethane/methanol 99:1->95:5)

Sources & evidence

ORD record
ord-d8b9a8eb0ea44862ac9741115adeb8ae
Source dataset
uspto-grants-2012_03
Patent number
US08138178B2

Linked notes

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