o-Iodonitrobenzene → HCID 24821449, compound

HRID 1931274Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]([O:15][C:16](=[O:31])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH3:14])([CH3:13])[CH3:12]>>[C:11]([O:15][C:16](=[O:31])[CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=[C:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH3:14])([CH3:13])[CH3:12]

Participants

Reactant 2

HCID 69115o-Iodonitrobenzene

HCID 4429378HCID 4429378, compound

Product 1

HCID 24821449HCID 24821449, compoundYield 38%

Procedure

Method A applied to 1-iodo-2-nitrobenzene (125 mg, 0.5 mmol) and 5-octanoylamino-pentanoic acid tert-butyl ester (180 mg, 0.6 mmol) yielded the title compound as yellowy oil (40 mg, 38%). 1H NMR (DMSO) δ 0.86 (t, J=6.8Hz, 3H), 1.22-1.86 (m, 23H), 2.27 (t, J=7.3, 2H), 3.14 (t, J=7.8Hz, 2H), 4.43 (t, J=7.2Hz), 7.49-7.54 (m, 2H), 7.77 (d, J=8.8Hz, 1H), 7.93 (d, J=8.8Hz).

Sources & evidence

ORD record: ord-6230252784e54536aff9844f91d70d41
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188282B2

Reaction notes

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