1,1'-Carbonyldiimidazole → N3-(tert-butoxycarbonyl)-N3-methyl-N-[4-(triphenylphosphonio) butyl]-beta-alaninamide bromide

HRID 58337Notes

Reaction equation

HRID 58337 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:14])[CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[Br-:27].[NH2:28][CH2:29][CH2:30][CH2:31][CH2:32][P+:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C)C=O.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH3:14])[CH2:9][CH2:10][C:11]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][P+:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4].[Br-:27]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27609523-(Methylamino)propanoic acid, N-BOC protectedHCID 10201848(4-Aminobutyl)(triphenyl)phosphonium bromide

Product 1

HCID 131737008N3-(tert-butoxycarbonyl)-N3-methyl-N-[4-(triphenylphosphonio) butyl]-beta-alaninamide bromideYield 116.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-(tert-butoxycarbonyl)-N-methyl-β-alanine (Matrix Scientific, 368 mg, 1.81 mmol) was dissolved in N,N-dimethylformamide (3.7 mL) and treated with N,N-carbonyldiimidazole (308 mg, 1.90 mmol). The reaction mixture was stirred at room temperature for 30 minutes. (4-Aminobutyl)(triphenyl)phosphonium bromide (1.12 g, 2.72 mmol) was added, and the reaction was stirred overnight at room temperature. The reaction 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 (1.26 g, 100%, 86% pure) 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-cdb50267135e41e7bd059917746c5047
Source dataset
uspto-grants-2016_09
Patent number
US09434753B2

Reaction notes

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