Potassium Carbonate → HCID 71133753, compound

HRID 1523115Notes

Reaction equation

HRID 1523115 reaction equation
[C:1]([CH2:8][N:9]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16][N:15]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+:29]([C:32]1[CH:40]=[CH:39][C:35]([CH2:36][CH2:37]Br)=[CH:34][CH:33]=1)([O-:31])=[O:30].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[C:22]([CH2:21][N:15]1[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])[CH2:20][CH2:19][N:18]([CH2:37][CH2:36][C:35]2[CH:34]=[CH:33][C:32]([N+:29]([O-:31])=[O:30])=[CH:40][CH:39]=2)[CH2:17][CH2:16]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 3938811,7-Bis(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane

Product 1

HCID 71133753HCID 71133753, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of compound (20) (1.56 g, 3.89 mmol), 4-nitrophenethyl bromide (1.79 g, 7.78 mmol), anhydrous K2CO3 (1.61 g, 11.67 mmol) and KI (1.94 g, 11.67 mmol) dissolved in dry toluene (150 ml) was stirred 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 (25) as a yellow oil (1.46 g, 68% yield).

Workup

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

Sources & evidence

ORD record
ord-7e227f1521bb45d5a7d23734cf663c05
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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