HCID 118365860, compound → HCID 118365855, compound

HRID 522193Notes

Reaction equation

HRID 522193 reaction equation
[CH2:1]([CH:7]([O:30][C:31](=[O:41])[C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-])=O)=[CH:34][CH:33]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>C(OCC)(=O)C.CN(C=O)C.[Ni]>[NH2:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]([O:30][C:31](=[O:41])[C:32]2[CH:33]=[CH:34][C:35]([NH2:38])=[CH:36][CH:37]=2)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[O:19])=[CH:26][CH:25]=1

Participants

5

Reactant 1

HCID 118365860HCID 118365860, compound

Product 1

HCID 118365855HCID 118365855, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
62.5 °C

Procedure

To a solution of 4-Nitro-benzoic acid 1-hexyl-11-(4-nitro-phenoxy carbonyl)-undecyl ester (290 g) in a mixture of Ethyl acetate (1.5 L) and DMF (300 mL) taken in a pressure vessel was added Raney Nickel (80 g). The reaction mixture was stirred under an atmosphere of Hydrogen (8-10 Kg) for 4 hours at a temperature of 60-65° C. The catalyst was removed by filtration. 75% of the solvent was distilled off and poured into cold water (2 L). The resulting solid was filtered off and washed with chilled water (100 mL) and do the slurry with 1 lit diisopropylether and filtered off, then dried the material properly in vacuum oven at 60-80° C. to yield pure 4-amino-benzoic acid 11-(4-amino-phenoxycarbonyl)-1-hexyl-undecyl ester product as off white powder (190 g) with a melting point of 156-159° C. The resulting compound was characterized by 1H NMR (CDCl3) δ 0.83 (t, 3H, CH3), 1.2-1.65 (m, 26H, 13×CH2), 1.81 (m, 2H, CH2), 2.12 (t, 2H, COCH2), 3.50 (m, 1H, CH), 5.5-6.1 (m, 4H, 2×NH2) 6.8-7.2 (m, 4H, Ar), 7.2-7.8 (m, 4H, Ar). The hydrolytic degradation of the compound was carried out in pH 9.0 buffer solution. The study showed that 1% solution is 100% hydrolyzed in 15 hours at 50° C.

Workup

  1. customtaken in a pressure vessel
  2. customThe catalyst was removed by filtration
  3. distillation75% of the solvent was distilled off
  4. additionpoured into cold water (2 L)
  5. filtrationThe resulting solid was filtered off
  6. washwashed with chilled water (100 mL)
  7. filtrationfiltered off
  8. customdried the material properly in vacuum oven at 60-80° C.

Sources & evidence

ORD record
ord-9591204ddde646469010004fb903d3d7
Source dataset
uspto-grants-2016_05
Patent number
US09328192B2

Reaction notes

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