HCID 86668962, compound → HCID 86668963, compound

HRID 877368Notes

Reaction equation

HRID 877368 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:11]([NH:13][CH2:14][CH:15]([OH:17])[CH3:16])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(#N)C.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:11]([NH:13][CH2:14][C:15](=[O:17])[CH3:16])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86668962HCID 86668962, compound

Product 1

HCID 86668963HCID 86668963, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of N2-(tert-butoxycarbonyl)-N-(2-hydroxypropyl)-D-alaninamide (13 g, 53 mmol) in acetonitrile (800 ml) and water (320 ml), was added RuCl3 (300 mg, 1.06 mmol) and NaBrO3 (4 g, 26.5 mmol). The resulting mixture was stirred at room temperature overnight. After concentration to remove most of acetonitrile, the residue was departed between water and ethyl acetate. The organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated to give 8.5 g (65.9%) of N2-(tert-butoxycarbonyl)-N-(2-oxopropyl)-D-alaninamide as solid. 1H-NMR CDCl3 δ 6.86 (br, 1H), 5.08 (br, 1H), 4.13 (s, 2H), 5.09 (s, 2H), 2.19 (s, 3H), 1.43 (s, 9H), 1.37 (s, 3H). ES-MS [M+1]+: 244.90

Workup

  1. concentrationAfter concentration
  2. customto remove most of acetonitrile
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-24dde07fb34c4a3396b5ef125ba2e719
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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