1,2-Dimethoxyethane → HCID 70571337, compound

HRID 2403575Notes

Reaction equation

HRID 2403575 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][NH:6][C:7](=[O:17])[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[CH:31][CH:30]=2)O1.[C:42](=O)([O-])[O-].[Na+].[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:42][N:6]([CH2:5][C:4]1[CH:3]=[C:2]([C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[CH:31][CH:30]=2)[CH:20]=[CH:19][CH:18]=1)[C:7](=[O:17])[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27953614-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholineHCID 68152809HCID 68152809, compound

Product 1

HCID 70571337HCID 70571337, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl {2-[(3-bromobenzyl)amino]-2-oxoethyl}carbamate (274 mg), 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine (222 mg), sodium carbonate (81 mg), tetrakis(triphenylphosphine)palladium (88 mg), DME (5 ml), and water (2.5 ml) were put into a 50-ml recovery flask, followed by stirring at 80° C. for 10 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The obtained residue was subjected to liquid separation with CHCl3 and water. The organic layer was separated, and then the aqueous layer was extracted with CHCl3 again. These organic layers were combined, dried over Na2SO4, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (2% MeOH/CHCl3) to obtain tert-butyl (2-{methyl[(4′-morpholin-4-ylbiphenyl-3-yl)methyl]amino}-2-oxoethyl)carbamate (270 mg) as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was subjected to liquid separation with CHCl3 and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with CHCl3 again
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-7efc02d6ca09422393e6b26276f099ea
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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