Toluene → HCID 58787888, compound

HRID 1375915Notes

Reaction equation

HRID 1375915 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C@@:5]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([CH3:22])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11](OS(C(F)(F)F)(=O)=O)=[CH:10][CH:9]=1)[CH3:2].[CH3:32][CH2:33][CH2:34]CB(O)O.C([O-])([O-])=O.[K+].[K+].[C:45]1([CH3:51])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[CH2:1]([O:3][C:4](=[O:31])[C@@:5]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([CH3:22])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:48]2[CH:49]=[CH:50][C:45]([CH2:51][CH2:32][CH2:33][CH3:34])=[CH:46][CH:47]=2)=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 20479Butylboronic AcidHCID 58787873HCID 58787873, compound

Product 1

HCID 58787888HCID 58787888, compound

Conditions

Temperature
95 °C

Procedure

(R)-2-tert-Butoxycarbonylamino-2-methyl-4-(4-trifluoromethane sulfonyloxy-phenyl)-butyric acid ethyl ester (100 mg), 4-butylboronic acid (75 mg) and K2CO3 (44 mg) are suspended in dry toluene (3 ml). Argon is bubbled through the mixture for 10 min., tetrakispalladiumtriphenyl-phosphine (5 mg) is added and the mixture is stirred at 95° C. under Argon for 16 h. After cooling to RT, ethyl acetate (5 ml) is added and the mixture is washed with 0.5N NaOH (2 ml), water (2 ml), 1M citric acid (2×2 ml) and water (2 ml). The organic phase is dried over MgSO4, the solvent removed and the crude material purified by chromatography using diethylether/hexane=1/5 (Rf=0.14, MS: (ES+): 454.6 (M+H)+).

Workup

  1. customArgon is bubbled through the mixture for 10 min.
  2. additiontetrakispalladiumtriphenyl-phosphine (5 mg) is added
  3. temperatureAfter cooling to RT
  4. additionethyl acetate (5 ml) is added
  5. washthe mixture is washed with 0.5N NaOH (2 ml), water (2 ml), 1M citric acid (2×2 ml) and water (2 ml)
  6. dry with materialThe organic phase is dried over MgSO4
  7. customthe solvent removed
  8. customthe crude material purified by chromatography

Sources & evidence

ORD record
ord-63236599f9564d96835f6da4852fb8be
Source dataset
uspto-grants-2007_01
Patent number
US07169817B2

Reaction notes

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