Potassium Phosphate, Tribasic → HCID 57708994, compound

HRID 547119Notes

Reaction equation

HRID 547119 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:5]1[CH:10]=[CH:9][C:8](Cl)=[CH:7][CH:6]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:58]([Si:62]([CH3:100])([CH3:99])[O:63][CH:64]([C:95]([CH3:98])([CH3:97])[CH3:96])[CH2:65][CH2:66][C:67]1[CH:72]=[CH:71][C:70]([C:73]([C:78]2[CH:83]=[CH:82][C:81](B3OC(C)(C)C(C)(C)O3)=[C:80]([CH3:93])[CH:79]=2)([CH2:76][CH3:77])[CH2:74][CH3:75])=[CH:69][C:68]=1[CH3:94])([CH3:61])([CH3:60])[CH3:59]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([C:81]2[CH:82]=[CH:83][C:78]([C:73]([C:70]3[CH:71]=[CH:72][C:67]([CH2:66][CH2:65][CH:64]([O:63][Si:62]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:99])[CH3:100])[C:95]([CH3:98])([CH3:97])[CH3:96])=[C:68]([CH3:94])[CH:69]=3)([CH2:74][CH3:75])[CH2:76][CH3:77])=[CH:79][C:80]=2[CH3:93])=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 56930596HCID 56930596, compoundHCID 577089262-[4-(1-{4-[3-(t-Butyldimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 57708994HCID 57708994, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

(R)-t-Butoxycarbonylamino-(4-chloro-phenyl)-acetic acid methyl ester (Example 167-(1); 37 mg, 0.124 mmol), palladium acetate (1.8 mg, 0.008 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (6.6 mg, 0.016 mmol), potassium phosphate (52 mg, 0.246 mmol) and water (0.2 mL) were added to a solution of 2-[4-(1-{4-[3-(t-butyldimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 24-(1); 50 mg, 0.082 mmol) in toluene (3 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for three hours. Then, the reaction mixture was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give the target compound as a colorless oil (28.5 mg, 47%).

Workup

  1. dry with materialThen, the reaction mixture was dried with anhydrous magnesium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-292bbd08f1274b829e047bba847d9fdc
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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