Triethylamine → (S)-Methyl 4-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate

HRID 72391Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.CO.CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:13]([O:12][C:11]([NH:10][C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([C:11]([O:12][CH3:13])=[O:17])=[CH:3][CH:4]=1)[CH3:9])=[O:17])([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (S)-tert-butyl (1-(4-bromophenyl)ethyl)carbamate (D1) (9.20 g, 27.3 mmol), 1,3-bis(diphenylphosphino)-propane (2.25 g, 5.46 mmol), palladium (II) acetate (1.22 g, 5.46 mmol), and triethylamine (11.5 ml, 81.9 mmol) in N,N-dimethylformamide/methanol (60 ml/60 ml) was stirred at 80° C. overnight under carbon monoxide atmosphere. After cooling to room temperature, the mixture was diluted with ether (300 ml) and washed with water (3×100 ml). The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 5:1 to afford the title compound (D2) (6.72 g) as white solid.

Workup

temperatureAfter cooling to room temperature
washwashed with water (3×100 ml)
dry with materialThe organic layer was dried over Na2SO4
customevaporated in vacuo
customThe residue was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 5:1

Sources & evidence

ORD record: ord-b5675bee7ce140d7acfffb54da8569a9
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828987B2

Reaction notes

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