Methyl iodide → (S)-4-(tert-butoxycarbonylamino)-5-methoxy-N,N,N-trimethyl-5-oxopentan-1-aminium iodide

HRID 83931Notes

Reaction equation

HRID 83931 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:20][CH3:21]>C1COCC1>[I-:20].[C:1]([O:5][C:6]([NH:8][C@H:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:14][CH2:15][CH2:16][N+:17]([CH3:21])([CH3:19])[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 58797552HCID 58797552, compound

Product 1

HCID 86702241(S)-4-(tert-butoxycarbonylamino)-5-methoxy-N,N,N-trimethyl-5-oxopentan-1-aminium iodide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 2-(tert-butoxycarbonylamino)-5-(dimethylamino)pentanoate (5.62 g, 20.5 mmol, 1.0 eq) in THF (40 mL), was added iodomethane (1.4 mL, 22.5 mmol, 1.1 eq). The mixture was stirred at room temperature for 1 h, until the starting material was consumed as determined by LCMS analysis. The reaction mixture was concentrated and then dried under high vacuum to provide (S)-4-(tert-butoxycarbonylamino)-5-methoxy-N,N,N-trimethyl-5-oxopentan-1-aminium iodide as a white solid, which was used in the next step without purification. MS (EI) m/z 289 (M+).

Workup

  1. customwas consumed
  2. concentrationThe reaction mixture was concentrated
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-4de7ca38eed24be592498768e2f9f8cc
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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