Triethylamine → HCID 71133775, compound

HRID 1523107Notes

Reaction equation

HRID 1523107 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][N:12]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20][N:19]([CH2:26][C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N+:44]([C:47]1[CH:54]=[CH:53][C:50]([CH2:51]Br)=[CH:49][CH:48]=1)([O-:46])=[O:45]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([CH2:11][N:12]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20][N:19]([CH2:26][C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:18][CH2:17][CH2:16][N:15]([CH2:51][C:50]2[CH:53]=[CH:54][C:47]([N+:44]([O-:46])=[O:45])=[CH:48][CH:49]=2)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 68106200HCID 68106200, compound

Product 1

HCID 71133775HCID 71133775, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of compound (4) (1.17 g, 2.36 mmol) in dry CHCl3 (50 ml) were added triethylamine (0.99 ml, 0.72 g, 7.08 mmol) and 4-nitrobenzyl bromide (0.51 g, 2.36 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 acetate and methanol (10:2) gave a purified clear oil, which was then solidified to obtain compound (15) (1.13 g, 76% yield). 1H NMR (500 MHz, CDCl3): δ 8.12-8.10 (dd, 2H), 7.51-7.49 (dd, 2H), 7.34-7.27 (m, 10H), 5.11 (s, 2H), 5.05 (s, 2H), 3.55 (s, 2H), 3.39 (s, 2H), 3.34 (s, 2H), 2.81 (brs, 2H), 2.74-2.72 (m, 4H), 2.67-2.64 (m, 6H), 2.59-2.57 (m, 2H), 2.46-2.44 (m, 2H), 1.71 (brs, 2H), 1.61-1.59 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 171.3, 170.8, 148.1, 146.9, 135.7, 129.3, 128.5, 128.2, 128.1, 123.3, 66.0, 65.8, 58.1, 55.5, 53.6, 53.1, 52.5, 52.0, 51.2, 49.6, 47.9, 47.2, 25.7; HRMS (FAB) calculated for C35H46N5O6: 632.3448 [(M+H)+], measured value: 632.3447 [(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 acetate and methanol (10:2)
  5. customgave a purified clear oil, which

Sources & evidence

ORD record
ord-fc9e5e91f5b34e5ca2f46786c1b674b5
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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