Hydrochloric Acid → tert-butyl 3-[4'-(2-Carboxy-ethyl)-biphenyl-4-yl]-propionate

HRID 562542Notes

Reaction equation

HRID 562542 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][CH:3]=1.[C:17]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([OH:19])=[O:18].C([O-])([O-])=O.[K+].[K+].Cl>C(#N)C.O.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(OCC)(=O)C>[C:17]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][CH:3]=2)=[CH:24][CH:23]=1)([OH:19])=[O:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 38634844-(2-Carboxyethyl)benzeneboronic acidHCID 10708234326496-52-0

Product 1

HCID 66724435tert-butyl 3-[4'-(2-Carboxy-ethyl)-biphenyl-4-yl]-propionate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

Tert-butyl 3-(4-bromophenyl)propionate (433 mg, 1.52 mmol) in acetonitrile-water (3:1, 13 ml) under argon atmosphere was treated with 4-(2-carboxyethyl)benzeneboronic acid (294 mg, 1.52 mmol), K2CO3 (251 mg, 1.82 mmol) and (Ph3P)4Pd (87 mg, 73 μmol), and the stirred mixture was heated at 90° C. for 4 hours. Excess ethyl acetate and 2 M HCl was added and the organic phase was washed with 2×2 M HCl and 2× water. Drying over MgSO4 and evaporation in vacuo gave the crude product, which was purified by chromatography on silica column eluted with ethyl acetate/hexane/acetic acid 50:50:1 to provide tert-butyl 3-[4′-(2-Carboxy-ethyl)-biphenyl-4-yl]-propionate, 330 mg (62%).

Workup

  1. washthe organic phase was washed with 2×2 M HCl and 2× water
  2. dry with materialDrying over MgSO4 and evaporation in vacuo
  3. customgave the crude product, which
  4. customwas purified by chromatography on silica column
  5. washeluted with ethyl acetate/hexane/acetic acid 50:50:1

Sources & evidence

ORD record
ord-b816e92ded954250ad8daa17a66f86cd
Source dataset
uspto-grants-2011_11
Patent number
US08067362B2

Reaction notes

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