HCID 10253545, compound → HCID 10002590, compound

HRID 1883649Notes

Reaction equation

HRID 1883649 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:17][C:18]1[CH:19]=[C:20]([CH:28]=[CH:29][C:30]=1[N+:31]([O-])=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CCOC(C)=O>[NH2:31][C:30]1[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])=[CH:19][C:18]=1[CH2:17][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 10253545HCID 10253545, compound

Product 1

HCID 10002590HCID 10002590, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 3-[[N-(tert-butoxycarbonyl)-N-phenethylamino]methyl]-4-nitrobenzoate (2.7 g, 5.9 mmole), 10% Pd/C (0.6 g, 0.6 mmole Pd), and EtOAc (60 mL) was shaken under H2 (50 psi). After 3 hr, the mixture was filtered to remove the catalyst, and the filtrate was concentrated to dryness. Flash chromatography on silica gel (20% EtOAc/hexanes) gave the title compound (2.3 g, 91%) as a yellow foamy oil which slowly partially solidified: 1H NMR (250 MHz, CDCl3) δ 7.74 (dd, J=8.4, 2.0 Hz, 1H), 7.67 (d, J=2.0 Hz, 1H), 7.05-7.40 (m, 5H), 6.57 (d, J=8.4 Hz, 1H), 5.00 (br s, 2H), 4.30 (s, 2H), 3.32 (app. t, 2H), 2.69 (app. t, 2H), 1.59 (s, 9H), 1.46 (s, 9H); MS (ES) m/e 449.2 (M+Na)+, 427.2 (M+H)+.

Workup

  1. filtrationthe mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-ce91a59a70af4782af5ccf9b62184cb6
Source dataset
uspto-grants-2004_07
Patent number
US06762201B1

Reaction notes

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