HCID 178443268, compound → Tert-Butyl 4-(trifluoromethyl)benzyl[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]carbamate

HRID 735830Notes

Reaction equation

HRID 735830 reaction equation
[C:1]([NH:14][O:15][C:16]([C:18]1[CH:43]=[CH:42][C:21]([CH2:22][N:23]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:20][CH:19]=1)=O)(=[NH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>N1C=CC=CC=1>[F:40][C:38]([F:41])([F:39])[C:35]1[CH:34]=[CH:33][C:32]([CH2:31][N:23]([CH2:22][C:21]2[CH:20]=[CH:19][C:18]([C:16]3[O:15][N:14]=[C:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[N:13]=3)=[CH:43][CH:42]=2)[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:37][CH:36]=1

Participants

3

Reactant 1

HCID 178443268HCID 178443268, compound

Product 1

HCID 67187080Tert-Butyl 4-(trifluoromethyl)benzyl[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]carbamateYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of tert-butyl 4-{[(dodecanimidoylamino)oxy]carbonyl}benzyl[4-(trifluoromethyl)benzyl]carbamate in pyridine was stirred under inert atmosphere at 120° C. for 4 h. The resulting brown solution was evaporated (under high vacuum) and the resulting oil was purified by column chromatography over silica gel (AcOEt/c-Hex 20/80) to give the title compound as a colorless oil (50 mg, 71%). 1H NMR (CDCl3, 300 MHz) δ 8.00 (d, J=8.1 Hz, 2H), 7.51 (d, J=8.1 Hz, 2H), 7.35-7.14 (m, 4H), 4.43 (s, 2H), 4.35 (s, 2H), 2.71 (t, J=7.5 Hz, 2H), 1.80-1.65 (m, 2H), 1.41 (s, 9H), 1.36-1.12 (m, 16H), 0.89 (t, J=7.0 Hz, 3H)

Workup

  1. customThe resulting brown solution was evaporated (under high vacuum)
  2. customthe resulting oil was purified by column chromatography over silica gel (AcOEt/c-Hex 20/80)

Sources & evidence

ORD record
ord-9edc0abef5df4993802424cd5a27dd8c
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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