Potassium Carbonate → (S)-tert-Butyl 4-(1-amino-3-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216941

Reaction equation

[NH2:1][C:2](=[O:37])[C@@H:3]([NH:20][C:21]([C:23]1([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][CH:6]=1.Br[C:39]1[CH:40]=[CH:41][C:42]2[O:46][C:45](=[O:47])[N:44]([CH3:48])[C:43]=2[CH:49]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:1][C:2](=[O:37])[C@@H:3]([NH:20][C:21]([C:23]1([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1)=[O:22])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:39]2[CH:40]=[CH:41][C:42]3[O:46][C:45](=[O:47])[N:44]([CH3:48])[C:43]=3[CH:49]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 75 °C

Procedure

(S)-tert-Butyl 4-(1-amino-1-oxo-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 16, step (i), 224 mg) in acetonitrile (10 mL) under nitrogen was treated with 5-bromo-3-methylbenzo[d]oxazol-2(3H)-one (99 mg) followed by an aqueous solution of potassium carbonate (2M, 0.433 mL) and 1,1 bis(bi-tert-butylphosphino)ferrocene palladium dichloride (6 mg). The reaction mixture was stirred at 75° C. for 18 h and then evaporated to an oil, dissolved in dichloromethane and absorbed onto silica. Purification by chromatography on silica eluting with 50% ethyl acetate in isohexane and then 100% ethyl acetate afforded the sub-titled compound (150 mg).

Workup

customevaporated to an oil
dissolutiondissolved in dichloromethane
customabsorbed onto silica
customPurification by chromatography on silica eluting with 50% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-16925092c566415492009b72895e3993
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193239B2

Linked notes

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