1,1'-Carbonyldiimidazole → 8,8,11,14,14-Pentamethyl-7,12-dioxo-1,1,1-triphenyl-13-oxa-6,11-diaza-1-phosphoniapentadecane bromide

HRID 58343Notes

Reaction equation

HRID 58343 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:17])[CH2:9][CH2:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[Br-:30].[NH2:31][CH2:32][CH2:33][CH2:34][CH2:35][P+:36]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C)C=O.C(Cl)Cl>[Br-:30].[CH3:15][C:11]([CH3:16])([CH2:10][CH2:9][N:8]([CH3:17])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:12](=[O:14])[NH:31][CH2:32][CH2:33][CH2:34][CH2:35][P+:36]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 10201848(4-Aminobutyl)(triphenyl)phosphonium bromideHCID 547544824-[(Tert-butoxycarbonyl)(methyl)amino]-2,2-dimethylbutanoic acid

Product 1

HCID 894633688,8,11,14,14-Pentamethyl-7,12-dioxo-1,1,1-triphenyl-13-oxa-6,11-diaza-1-phosphoniapentadecane bromideYield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-[(tert-butoxycarbonyl)(methyl)amino]-2,2-dimethylbutanoic acid (Organic and Molecular Chemistry, 2011, 9, 1846-1854, 117 mg, 0.48 mmol) was dissolved in N,N-dimethylformamide (1.2 mL) and treated with N,N-carbonyldiimidazole (104 mg, 0.64 mmol). The mixture was stirred at room temperature for 30 minutes. (4-Aminobutyl)(triphenyl)phosphonium bromide (277 mg, 0.67 mmol) was added, and the reaction was stirred overnight at room temperature. The reaction mixture was then diluted with methylene chloride and washed with 5% aqueous lithium chloride (3 times), 1N aqueous hydrogen chloride, and saturated sodium bicarbonate. The organic solution was dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound (210 mg, 69%) as a white foam. Sample was used crude in next step.

Workup

  1. stirringthe reaction was stirred overnight at room temperature
  2. washwashed with 5% aqueous lithium chloride (3 times), 1N aqueous hydrogen chloride, and saturated sodium bicarbonate
  3. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b462afc41980416ea4c8e455f09a0e8c
Source dataset
uspto-grants-2016_09
Patent number
US09434753B2

Reaction notes

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