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3-(2-Carboxyethyl)phenylboronic acid → 3-[2'-(1-tert-Butoxycarbonylamino-ethyl)-5'-(pyridin-4-ylcarbamoyl)-biphenyl-3-yl]-propionic acid

HRID 2409365
Notes
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Reaction equation

HRID 2409365 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:24])[NH:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:12][C:11]=1Br)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:27]([CH2:30][CH2:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)([OH:29])=[O:28]>COCCOC.CCO.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:1]([O:5][C:6]([NH:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:24])[NH:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:12][C:11]=1[C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([CH2:31][CH2:30][C:27]([OH:29])=[O:28])[CH:33]=1)[CH3:9])=[O:26])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 38561183-(2-Carboxyethyl)phenylboronic acidHCID 67408319{1-[2-Bromo-4-(pyridine-4-ylcarbamoyl)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 674223603-[2'-(1-tert-Butoxycarbonylamino-ethyl)-5'-(pyridin-4-ylcarbamoyl)-biphenyl-3-yl]-propionic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 20074477
Dimethoxyethane ethanol
Solvent

Conditions

Temperature
160 °C

Procedure

To a solution of {1-[2-bromo-4-(pyridine-4-ylcarbamoyl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (3122 μmol) in a mixture of DME/EtOH/2N Na2CO3: 1/1/1 (20 ml) were added 3-carboxyethylphenylboronic acid (1.5 eq) and Pd tetrakis (0.05 eq). The reaction mixture was heated in the microwave at 160° C. for 15 minutes. The reaction mixture was cooled to RT, filtered over celite and washed with EtOAc and MeOH. The solvents were removed under reduced pressure. The compound was purified by column chromatography (silicagel, DCM/MeOH gradient).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered over celite
  3. washwashed with EtOAc and MeOH
  4. customThe solvents were removed under reduced pressure
  5. customThe compound was purified by column chromatography (silicagel, DCM/MeOH gradient)

Sources & evidence

ORD record
ord-d0257c6fe70e48c58378d16c13d245ca
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08815873B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes