L-Leucine → HCID 59444264, compound

HRID 1888114Notes

Reaction equation

HRID 1888114 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C:13]1([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.N[C@H](C(O)=O)CC(C)C.C(N(C(C)C)CC)(C)C.[O:42](C(OC(C)(C)C)=O)[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=O>O1CCOCC1>[C:46]([O:45][C:43]([NH:12][C:13]1([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)=[O:42])([CH3:49])([CH3:48])[CH3:47]

Participants

6

Reactant 4

HCID 6106L-LeucineHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 86644200HCID 86644200, compound

Product 1

HCID 59444264HCID 59444264, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 2-(4-aminotetrahydro-2H-pyran-4-yl)acetate p-toluenesulfonic acid salt (prepared in the similar manner as described in Bioorg. Med. Chem. Leu. 2006, 16, 2699-2704, 1.0 g, 2.9 mmol) in anhydrous dioxane (5 mL) was sequentially added diisopropylethylamine (1 mL, 5.8 mmol) and (BOC)2O (1.26 g, 5.8 mmol) at room temperature. Upon completion of addition, the reaction mixture was stirred at room temperature for 60 h, concentrated under reduced pressure and partitioned between ethyl acetate (30 mL) and 1N HCl (10 mL). The ethyl acetate layer was washed with 1N NaOH (10 mL), brine (10 mL), dried over sodium sulfate and concentrated under reduced pressure to yield the title compound (1.0 g) as an oil, which was used in the next step without further purification.

Workup

  1. customat room temperature
  2. additionUpon completion of addition
  3. concentrationconcentrated under reduced pressure
  4. custompartitioned between ethyl acetate (30 mL) and 1N HCl (10 mL)
  5. washThe ethyl acetate layer was washed with 1N NaOH (10 mL), brine (10 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c965a187268f4cdbb352e2d54f0420ee
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

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