Methyl iodide → (R)-3-[8-(3,4-difluoro-benzyloxy)-octanoylamino]-4-trimethylammonio-butyrate

HRID 1802992Notes

Reaction equation

HRID 1802992 reaction equation
[C:1](=O)([O-])O.[K+].IC.[F:8][C:9]1[CH:10]=[C:11]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([NH:23][C@@H:24]([CH2:29][N:30]([CH3:32])[CH3:31])[CH2:25][C:26]([OH:28])=[O:27])=[O:22]>CO.C(Cl)(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([NH:23][C@@H:24]([CH2:29][N+:30]([CH3:1])([CH3:32])[CH3:31])[CH2:25][C:26]([O-:28])=[O:27])=[O:22]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 516893Potassium BicarbonateHCID 46223510(R)-3-[8-(3,4-difluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid

Product 1

HCID 44465161(R)-3-[8-(3,4-difluoro-benzyloxy)-octanoylamino]-4-trimethylammonio-butyrate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Potassium hydrogencarbonate (24 mg, 0.24 mmol) and iodomethane (106 mg, 0.74 mmol) were added to a solution of (R)-3-[8-(3,4-difluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid (77 mg, 0.19 mmol) in methanol (2.5 mL). The reaction mixture was stirred at room temperature for 16 h, then diluted with chloroform (5 mL). Insoluble material was removed by filtration to afford (R)-3-[8-(3,4-difluoro-benzyloxy)-octanoylamino]-4-trimethylammonio-butyrate as a light yellow solid, m/e=429.3 ([M+H]+).

Workup

  1. customInsoluble material was removed by filtration

Sources & evidence

ORD record
ord-7d5cae9ff22a48c396ff3364c61428b5
Source dataset
uspto-grants-2013_01
Patent number
US08349893B2

Reaction notes

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