Triethylamine → (R)-2-(1H-imidazole-1-sulfonamido)-4-methoxy-N,N,N-trimethyl-4-oxobutan-1-aminium chloride

HRID 1958723Notes

Reaction equation

HRID 1958723 reaction equation
[Cl-:1].[NH2:2][C@H:3]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C.[O-]S(C(F)(F)F)(=O)=O.[N:29]1([S:34](N2C=C[N+](C)=C2)(=[O:36])=[O:35])[CH:33]=[CH:32][N:31]=[CH:30]1>CC#N>[Cl-:1].[N:29]1([S:34]([NH:2][C@H:3]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:4][N+:5]([CH3:8])([CH3:6])[CH3:7])(=[O:36])=[O:35])[CH:33]=[CH:32][N:31]=[CH:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117281493-(Imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflateHCID 86641220(R)-2-amino-4-methoxy-N,N,N-trimethyl-4-oxobutan-1-aminium chloride

Product 1

HCID 68743870(R)-2-(1H-imidazole-1-sulfonamido)-4-methoxy-N,N,N-trimethyl-4-oxobutan-1-aminium chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (R)-2-amino-4-methoxy-N,N,N-trimethyl-4-oxobutan-1-aminium chloride (35 mg) in anhydrous MeCN (5 mL) is treated with triethyl amine (2.5 equiv.) and 3-(Imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate (1.5 equiv.). The reaction mixture is stirred at ambient temperature for 16 h then concentrated under reduced pressure and the resulting residue is purified on silica gel using MeOH/DCM (0->80%).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customthe resulting residue is purified on silica gel

Sources & evidence

ORD record
ord-682aef7c5b9c4c7bb0e1857df13798f4
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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