2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl 4-nitrobenzoate → 2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl 4-aminobenzoate

HRID 1159432Notes

Reaction equation

HRID 1159432 reaction equation
[N+:1]([C:4]1[CH:32]=[CH:31][C:7]([C:8]([O:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][CH:18]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])=[O:9])=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][CH:18]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])=[O:9])=[CH:31][CH:32]=1

Participants

4

Reactant 1

HCID 595143922-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl 4-nitrobenzoate

Product 1

HCID 595143802-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl 4-aminobenzoateYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl 4-nitrobenzoate (7.47 g, 17 mmoles) in 1 liter of ethyl acetate, containing 1.5 g of 10% Pd on carbon (wet) is evacuated and filled with H2 twice. The mixture is subjected to hydrogen at 1 atmosphere of pressure for two hours. The catalyst is filtered off on a Celite pad and the solution is concentrated in vacuo, yielding a yellow oil. Purification on silica gel using a gradient of 30-45% ethyl acetate in hexanes provided 5.436 g (80%) of the title compound as a white solid. 400 MHz 1H NMR (CDCl3) δ: 7.86 (d, J=8.4 Hz, 2H), 7.75 (d, J=7.3 Hz, 2H), 7.58 (d, J=7.3 Hz, 2H), 7.39 (t, J=7.3 Hz, 2H), 7.30 (t, J=7.5 Hz, 1H), 6.64 (d, J=8.4 Hz, 2H), 5.13 (br. t, 1H), 4.40 (d, J=7.0 Hz, 2H), 4.36 (t, J=5.1 Hz, 2H), 4.22 (t, J=7.0 Hz, 1H), 4.1-4.0 (br. s, 2H), 3.65-3.55 (m, 2H). LCMS: 403 [M+H].

Workup

  1. customis evacuated
  2. additionfilled with H2 twice
  3. filtrationThe catalyst is filtered off on a Celite pad
  4. concentrationthe solution is concentrated in vacuo
  5. customyielding a yellow oil
  6. customPurification on silica gel using a gradient of 30-45% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e5ab449ef1f44722972fcdaa80b7e1db
Source dataset
uspto-grants-2010_10
Patent number
US07812051B2

Reaction notes

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