Ethanol → 3-(4'-Benzo[1,3]dioxol-5-yl-biphenyl-4-ylmethylsulfanyl)-2-tert-butoxycarbonyl amino-propionic Acid Methyl Ester

HRID 900361Notes

Reaction equation

HRID 900361 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH:4]([NH:21]C(OC(C)(C)C)=O)[CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.[CH2:30]1[O:38][C:37]2[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][C:32]=2[O:31]1.C(O)C.[C:45]([O-:48])([O-])=[O:46].[Na+].[Na+].[C:51]1([CH3:57])[CH:56]=CC=C[CH:52]=1>C(OCC)(=O)C.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>[CH3:1][O:2][C:3](=[O:29])[C:4]([NH2:21])([C:45]([O:48][C:51]([CH3:57])([CH3:56])[CH3:52])=[O:46])[CH2:5][S:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[CH:16][C:17]([C:35]3[CH:34]=[CH:33][C:32]4[O:31][CH2:30][O:38][C:37]=4[CH:36]=3)=[CH:18][CH:19]=2)=[CH:12][CH:13]=1

Participants

8

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 688180613-(4'-Bromobiphenyl-4-ylmethylsulfanyl)-2-tert-butoxycarbonylamino-propionic Acid Methyl Ester

Product 1

HCID 688197533-(4'-Benzo[1,3]dioxol-5-yl-biphenyl-4-ylmethylsulfanyl)-2-tert-butoxycarbonyl amino-propionic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(4′-bromobiphenyl-4-ylmethylsulfanyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester, 0.26 g (0.54 mmol), 3,4-methylenedioxyphenylboronic acid, 90 mg (0.54 mmol), Pd(PPh3)4, 63 mg (0.054 mmol), in 5 mL of toluene and 3 mL of ethanol was heated to obtain a clear solution. To the solution was added 5 mL of 0.4M aq. Na2CO3. The reaction mixture refluxed for 4 h at 80° C. The mixture was cooled to room temperature and diluted with 100 mL ethyl acetate. The organic layer was washed with 2×50 mL portions of water, 2×50 mL portions of sat. aq. NaCl, and dried (MgSO4). After the solution was concentrated, the residue was purified by column chromatography (eluted with 7% EtOAc-Heptane) to afford the desired product in 0.13 g (46%) as a white solid. 1H NMR (CDCl3) 7.64-7.56 (m, 6H), 7.38 (d, 2H, J=9.3 Hz), 7.10 (dd, 2H, J=6.7, 2.0 Hz), 6.90 (d, 1H, J=9.3 Hz), 6.01 (s, 2H), 5.32 (d, 1H, J=8.0 Hz), 4.63-4.52 (m, 1H), 3.78 (s, 2H), 3.76 (s, 3H), 2.95 (dd, 1H, J=15.7, 5.3 Hz), 2.85 (dd, 1H, J=15.7, 6.3 Hz), 1.47 (s, 9H).

Workup

  1. customto obtain a clear solution
  2. temperatureThe mixture was cooled to room temperature
  3. washThe organic layer was washed with 2×50 mL portions of water, 2×50 mL portions of sat. aq. NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationAfter the solution was concentrated
  6. customthe residue was purified by column chromatography (eluted with 7% EtOAc-Heptane)

Sources & evidence

ORD record
ord-88713f67d236429a8d9b51bd8f257462
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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