1,4-Dioxane hydrochloride → (2R,4S)-2-Aminomethyl-4-ethyl-heptanoic Acid

HRID 132616Notes

Reaction equation

HRID 132616 reaction equation
COC([N:5]1[CH2:10][C@@H:9]([CH2:11][C@@H:12]([CH2:16][CH3:17])[CH2:13][CH2:14][CH3:15])[C:8](=[O:18])N(C)[C@@H]1C(C)(C)C)=O.Cl.[O:25]1CCOCC1>>[NH2:5][CH2:10][C@@H:9]([CH2:11][C@@H:12]([CH2:16][CH3:17])[CH2:13][CH2:14][CH3:15])[C:8]([OH:18])=[O:25]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69269257(2S,5R)-2-tert-Butyl-5-((S)-2-ethyl-pentyl)-3-methyl-4-oxo-tetrahydro-pyrimidine-1-carboxylic Acid Methyl Ester

Product 1

HCID 86597954(2R,4S)-2-Aminomethyl-4-ethyl-heptanoic AcidYield 57%

Conditions

Temperature
105 °C

Procedure

A stirred solution of (2S,5R)-2-tert-butyl-5-((S)-2-ethyl-pentyl)-3-methyl-4-oxo-tetrahydro-pyrimidine-1-carboxylic acid methyl ester (0.185 g, 0.567 mmol) in a 1:1 mixture of 6N HCl/dioxane (8 mL) was heated at 105° C. for 6 days. The reaction was cooled to room temperature and concentrated under reduced pressure. The product was dissolved in 1:1 MeOH/H2O and loaded onto an ion exchange chromatography column (Varian SCX-Prepacked 10 g, 60 mL) and eluted with 1:1 MeOH/H2O (95%)+NH4OH. The fractions containing product were collected and concentrated under reduced pressure to yield 0.06 g (57%) of product: 1H NMR (400 MHz, CD3OD) δ ppm 0.9 (m, 6H), 1.3 (m, 5H), 1.4 (m, 3H) 1.7 (m, 1H), 2.5 (m, 1H), 2.9 (d, J=6.6 Hz, 2H). MS: M+1 (188).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe product was dissolved in 1:1 MeOH/H2O
  4. washeluted with 1:1 MeOH/H2O (95%)+NH4OH
  5. additionThe fractions containing product
  6. customwere collected
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-061d5249970a4aebb73634fc357a5336
Source dataset
uspto-grants-2008_06
Patent number
US07388023B2

Reaction notes

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