Sodium Carbonate → HCID 59635746, compound

HRID 470556Notes

Reaction equation

HRID 470556 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][N:11]([CH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[C:10](=[O:20])[CH:9]=1.[OH:21][C:22]([CH3:55])([CH3:54])[CH2:23][C@@:24]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:29][C:28](=[O:30])[N:27]([C@H:31]([C:33]2[CH:38]=[CH:37][C:36](B3OC(C)(C)C(C)(C)O3)=[CH:35][CH:34]=2)[CH3:32])[CH2:26][CH2:25]1>CN(C)C=O>[OH:17][CH2:16][C:15]([CH3:19])([CH3:18])[CH2:14][N:11]1[CH:12]=[CH:13][C:8]([C:36]2[CH:35]=[CH:34][C:33]([C@@H:31]([N:27]3[CH2:26][CH2:25][C@:24]([CH2:23][C:22]([OH:21])([CH3:54])[CH3:55])([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[O:29][C:28]3=[O:30])[CH3:32])=[CH:38][CH:37]=2)=[CH:9][C:10]1=[O:20]

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 59635786HCID 59635786, compound

Product 1

HCID 59635746HCID 59635746, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2 M aqueous Na2CO3 solution (0.32 mL) was added to a mixture of 4-bromo-1-(3-hydroxy-2,2-dimethyl-propyl)-1H-pyridin-2-one (0.13 g) and (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 (0.15 g) in N,N-dimethylformamide (3 mL). The resulting mixture was sparged with argon for 5 min, before [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (26 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 water and brine and dried (MgSO4). The solvent was evaporated and the residue was purified by HPLC on reversed phase (methanol/water/NH4OH) to afford the title compound as a beige solid. Yield: 0.10 g (60% of theory); Mass spectrum (ESI+): m/z=533 [M+H]+.

Workup

  1. customThe resulting mixture was sparged with argon for 5 min, before [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (26 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 water and brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated
  9. customthe residue was purified by HPLC on reversed phase (methanol/water/NH4OH)

Sources & evidence

ORD record
ord-e3038868bd8e4ae2b7ab9d01353825f7
Source dataset
uspto-grants-2014_01
Patent number
US08629138B2

Reaction notes

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