Potassium Carbonate → HCID 71133877, compound

HRID 1523105Notes

Reaction equation

HRID 1523105 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].[N+:31]([C:34]1[CH:42]=[CH:41][C:37]([CH2:38][CH2:39]Br)=[CH:36][CH:35]=1)([O-:33])=[O:32].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[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]([CH2:39][CH2:38][C:37]2[CH:36]=[CH:35][C:34]([N+:31]([O-:33])=[O:32])=[CH:42][CH:41]=2)[CH2:18][CH2:17]1)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 68106176HCID 68106176, compound

Product 1

HCID 71133877HCID 71133877, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of compound (5) (1.37 g, 3.19 mmol), 4-nitrophenethyl bromide (1.47 g, 6.38 mmol), anhydrous K2CO3 (1.32 g, 9.57 mmol) and KI (1.59 g, 9.57 mmol) dissolved in dry toluene (150 ml) was stirred under reflux for 24 hours. The solvent was evaporated from the reaction mixture under reduced pressure, and CH2Cl2 (250 ml) was added thereto. The resultant brown slurry was filtered through a celite pad, and washed with CH2Cl2 (2×30 ml). The solvent was evaporated from the combined filtrate under reduced pressure. The residue thus obtained was purified via alumina (basic) column chromatography using EtOAc/methanol (10:2) as an eluent to provide compound (8) as a yellow oil (1.26 g, 68% yield). 1H NMR (500 MHz, CDCl3): δ 8.07-8.06 (dd, 2H), 7.35-7.33 (dd, 2H), 3.23-3.20 (dd, 4H), 2.97 (brs, 4H), 2.87-2.82 (m, 4H), 2.71-2.51 (m, 12H), 1.88 (brs, 2H), 1.61 (brs, 2H), 1.39-1.37 (dd, 18H); 13C NMR (125 MHz, CDCl3): δ 170.7, 170.5, 148.6, 146.3, 129.5, 123.5, 81.3, 81.1, 55.7, 55.3, 55.0, 52.5, 52.0, 50.2, 49.5, 48.4, 46.1, 32.0, 28.1, 24.4, 24.3, 23.2; HRMS (FAB) calculated for C30H52N5O6: 578.3918 [(M+H)+], measured value: 578.3915 [(M+H)+].

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe solvent was evaporated from the reaction mixture under reduced pressure, and CH2Cl2 (250 ml)
  3. additionwas added
  4. filtrationThe resultant brown slurry was filtered through a celite pad
  5. washwashed with CH2Cl2 (2×30 ml)
  6. customThe solvent was evaporated from the combined filtrate under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified via alumina (basic) column chromatography

Sources & evidence

ORD record
ord-468d729691b44e4982fb51a5926ac7fb
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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