Triethylamine → HCID 71133754, compound

HRID 1523103Notes

Reaction equation

HRID 1523103 reaction equation
[C:1]([CH2:8][N:9]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][N:16]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[N+:38]([C:41]1[CH:48]=[CH:47][C:44]([CH2:45]Br)=[CH:43][CH:42]=1)([O-:40])=[O:39]>C(Cl)(Cl)Cl>[C:24]([CH2:23][N:16]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10][N:9]([CH2:8][C:1]([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2])[CH2:22][CH2:21][CH2:20][N:19]([CH2:45][C:44]2[CH:47]=[CH:48][C:41]([N+:38]([O-:40])=[O:39])=[CH:42][CH:43]=2)[CH2:18][CH2:17]1)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 68106176HCID 68106176, compound

Product 1

HCID 71133754HCID 71133754, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of compound (5) (1.27 g, 2.96 mmol) in dry CHCl3 (50 ml) were added triethylamine (1.21 ml, 0.90 g, 8.88 mmol) and 4-nitrobenzyl bromide (0.64 g, 2.96 mmol). After stirring at an ambient temperature for 10 hours, the solvent was removed under reduced pressure, and the residue was purified through column chromatography on alumina (basic). Extraction with a mixture of ethyl acetate and methanol (10:2) gave a purified clear oil, which was then solidified to obtain compound (7) (1.30 g, 78% yield). 1H NMR (500 MHz, CDCl3): δ 8.11-8.10 (dd, 2H), 7.55-7.53 (dd, 2H), 3.56 (s, 2H), 3.24 (s, 2H), 3.20-3.06 (m, 6H), 3.01 (brs, 2H), 2.70-2.58 (m, 4H), 2.54-2.42 (m, 4H), 2.39 (brs, 2H), 1.93 (brs, 2H), 1.75 (brs, 2H), 1.39-1.36 (dd, 18H); 13C NMR (125 MHz, CDCl3): δ 171.3, 170.5, 147.0, 146.6, 130.1, 123.3, 81.9, 81.2, 58.1, 56.4, 55.8, 54.9, 53.1, 51.6, 51.5, 51.2, 49.6, 48.5, 46.1, 28.0, 25.1, 22.7; HRMS (FAB) calculated for C29H50N5O6: 564.3761 [(M+H)+], measured value: 564.3757 [(M+H)+].

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was purified through column chromatography on alumina (basic)
  3. extractionExtraction
  4. additionwith a mixture of ethyl acetate and methanol (10:2)
  5. customgave a purified clear oil, which

Sources & evidence

ORD record
ord-0b4122c3a5484333aceb2b221af3f9bf
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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