Sodium Carbonate → HCID 69103505, compound

HRID 2220430Notes

Reaction equation

HRID 2220430 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@H:19]([OH:26])[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[CH2:27]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:36]=1[C:37]([O:39][CH3:40])=[O:38])[CH:28]([CH3:30])[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:13]([O:12][C:11]([N:10]([CH2:18][C@H:19]([OH:26])[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:33]2[CH:34]=[CH:35][C:36]([C:37]([O:39][CH3:40])=[O:38])=[C:31]([CH2:27][CH:28]([CH3:30])[CH3:29])[CH:32]=2)=[CH:3][CH:4]=1)=[O:17])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24822809HCID 24822809, compoundHCID 67098073HCID 67098073, compound

Product 1

HCID 69103505HCID 69103505, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of tert-butyl [2-(4-bromophenyl)ethyl]-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (500 mg), [3-isobutyl-4-(methoxycarbonyl)phenyl]boronic acid (336 mg), [1,1′-bis(diphenylphosphino)feffocene]palladium(II) dichloride (48.5 mg) and 1,1′-bis(diphenylphosphino)ferrocene (16.4 mg) in N,N-dimethylformamide (3.75 ml) was added 2.0M aqueous sodium carbonate solution (2.08 ml) and the mixture was stirred at 90° C. for 3 hours. After cooling to room temperature, the mixture was partitioned between ethyl acetate (30 ml) and water (30 ml). The organic layer was separated, washed with brine (30 ml) and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave a crude product which was purified by column chromatography on silica gel (hexane/ethyl acetate=1/1 to 1/3) to give methyl 4′-[2-[[tert-butoxycarbonyl]-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]ethyl]-3-isobutyl-4-biphenylcarboxylate (395 mg) as a yellow solid (foam).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between ethyl acetate (30 ml) and water (30 ml)
  3. customThe organic layer was separated
  4. washwashed with brine (30 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration
  7. customfollowed by evaporation under reduced pressure
  8. customgave a crude product which
  9. customwas purified by column chromatography on silica gel (hexane/ethyl acetate=1/1 to 1/3)

Sources & evidence

ORD record
ord-effb71e5165f4623a43849138cdd0cb9
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

Loading…