4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-nitrobenzamido)methyl)phenyl 4-(heptyloxy)benzoate → 4-((4-amino-N-(2-(tert-butoxy)-2-oxoethyl)benzamido)methyl)phenyl 4-(heptyloxy)benzoate

HRID 923530Notes

Reaction equation

HRID 923530 reaction equation
[CH2:1]([O:8][C:9]1[CH:44]=[CH:43][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:24](=[O:34])[C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=3)=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]>C1COCC1.[Pd]>[CH2:1]([O:8][C:9]1[CH:44]=[CH:43][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:24](=[O:34])[C:25]3[CH:26]=[CH:27][C:28]([NH2:31])=[CH:29][CH:30]=3)=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 892531114-((N-(2-(tert-butoxy)-2-oxoethyl)-4-nitrobenzamido)methyl)phenyl 4-(heptyloxy)benzoate

Product 1

HCID 892531254-((4-amino-N-(2-(tert-butoxy)-2-oxoethyl)benzamido)methyl)phenyl 4-(heptyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Prepared using General Procedure 5: A solution of 4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-nitrobenzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-3 (888 mg, 1.47 mmol) in THF (15 mL) was hydrogenated in an H-Cube (55 mmol Pd/C cartridge, 1 mL/min, 15 mL volume). The reaction mixture was concentrated to provide 896 mg of crude 4-((4-amino-N-(2-(tert-butoxy)-2-oxoethyl)benzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-4. The crude material was carried forward without further purification. LCMS-ESI (m/z) calculated for C34H42N2O6: 574; found 475 [M+H-Boc]+, tR=3.48 min (Method 5). 1H NMR (400 MHz, CDCl3) δ 8.20-8.04 (m, 2H), 7.44-7.26 (m, 4H), 7.19 (d, J=8.1 Hz, 2H), 7.01-6.90 (m, 2H), 6.63 (d, J=8.3 Hz, 2H), 4.73 (s, 2H), 4.04 (t, J=6.6 Hz, 2H), 3.80-3.67 (m, 2H), 1.89-1.76 (m, 2H), 1.45 (s, 9H), 1.42-1.23 (m, 8H), 0.90 (t, J=6.9 Hz, 3H).

Workup

  1. customPrepared
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-ab3e36b7090341d28caf1b535dd1b3e3
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

Loading…