Sodium Carbonate → HCID 68749021, compound

HRID 333323Notes

Reaction equation

HRID 333323 reaction equation
Br[C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH:7]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:4][CH:3]=1.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[C:2]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:28]=[CH:27][C:5]([CH2:6][CH:7]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 68746130HCID 68746130, compound

Product 1

HCID 68749021HCID 68749021, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A solution of benzyl 2-(4-bromobenzyl)-3-(tert-butoxycarbonylamino)propanoate (44 mg, 0.098 mmol), phenylboronic acid (17.95 mg, 0.147 mmol), Pd(PPh3)4 (11.34 mg, 9.81 μmol) and 2M aqueous Na2CO3 (0.098 ml, 0.196 mmol) in toluene (1 ml) was allowed to stir under nitrogen at 95° C. for 18 hours. The reaction mixture was cooled to room temperature, and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 0:100) to give benzyl 3-(biphenyl-4-yl)-2-((tert-butoxycarbonylamino)methyl)propanoate (27.3 mg); Retention time=1.78 minutes (condition B); MS (m+1)=446.1.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 0:100)

Sources & evidence

ORD record
ord-84e7e26996be46288df91c80912e008b
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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