Triethylamine → HCID 67352530, compound

HRID 1676031Notes

Reaction equation

HRID 1676031 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C@@H:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(N(CC)CC)C>ClCCl>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:11][C@@H:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 738951-Fluoro-2-nitrobenzeneHCID 2733824HCID 2733824, compound

Product 1

HCID 67352530HCID 67352530, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-fluoronitrobenzene (150 mg, 1.06 mmol) in dichloromethane (4 mL) was added tert-butyl (3R)-3-amino-3-phenylpropanoate (235 mg, 1.06 mmol) and triethylamine (300 μL, 2.12 mmol). The solution was stirred at room temperature for 4 hours, and was then evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with dichloromethane, to afford the title compound, 1H NMR: (CD3OD), 8.76 (br m, 1H), 8.18 (d, J=7.69, 1H), 7.44 (d, J=7.69, 2H), 7.40-7.37 (m, 2H), 7.32-7.28 (m, 1H), 6.84 (d, J=8.79 1H), 6.73-6.69 (m, 1H), 5.12 (dd, J=13.18, 6.59 1H), 2.91 (d, J=6.59 2H), 1.41 (s, 9H).

Workup

  1. customwas then evaporated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-a51d0e9e44684a63abcc4dde385ab053
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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