Hydrochloric Acid → (S)-4-amino-5-methoxy-N,N,N-trimethyl-5-oxopentan-1-aminium chloride hydrochloride

HRID 83932Notes

Reaction equation

HRID 83932 reaction equation
[I-].C(OC([NH:9][C@H:10]([C:18]([O:20][CH3:21])=[O:19])[CH2:11][CH2:12][CH2:13][N+:14]([CH3:17])([CH3:16])[CH3:15])=O)(C)(C)C.[ClH:22]>O1CCOCC1>[ClH:22].[Cl-:22].[NH2:9][C@H:10]([C:18]([O:20][CH3:21])=[O:19])[CH2:11][CH2:12][CH2:13][N+:14]([CH3:16])([CH3:15])[CH3:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86702241(S)-4-(tert-butoxycarbonylamino)-5-methoxy-N,N,N-trimethyl-5-oxopentan-1-aminium iodide

Product 1

HCID 86702233(S)-4-amino-5-methoxy-N,N,N-trimethyl-5-oxopentan-1-aminium chloride hydrochlorideYield 106.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (S)-4-(tert-butoxycarbonylamino)-5-methoxy-N,N,N-trimethyl-5-oxopentan-1-aminium iodide (20.5 mmol, 1.0 eq) in anhyd dioxane (10 mL), was added HCl (51 mL, 205 mmol, 10 eq, 4M in dioxane). The orange slurry was stirred at room temperature for 1 h, the solids were broken up, then stirred vigorously for another 1 h. The suspension was allowed to settle before cannulating off the dioxane layer. The remaining yellow slurry was rinsed with Et2O, stirred and cannulated out the ether layer (4×). The solids were dried under high vacuum to give the title compound (5.68 g) as a light yellow powder. 1H NMR (400 MHz, DMSO) δ 8.75 (s, 3H), 4.03-3.93 (m, 1H), 3.68 (s, 3H), 3.30-3.20 (m, 2H), 2.98 (s, 9H), 1.89-1.69 (m, 4H); MS (EI) m/z 189 (M+).

Workup

  1. stirringstirred vigorously for another 1 h
  2. washThe remaining yellow slurry was rinsed with Et2O
  3. stirringstirred
  4. customThe solids were dried under high vacuum

Sources & evidence

ORD record
ord-b7e6eb2830d340549a9d288ad32699ed
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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