Pyridine → tert-Butyl (S)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate

HRID 1473714Notes

Reaction equation

HRID 1473714 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][CH:11]=[O:12])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 1049PyridineHCID 11054918(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

Product 1

HCID 10901762tert-Butyl (S)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-Butyl N-(tert-butoxycarbonyl)-L-homoserinate (1.00 g, 3.63 mmol) in dichloromethane (50 mL) was added at r.t. pyridine (0.88 mL, 10.9 mmol) and Dess-Martin-periodinane (2.31 g, 5.45 mmol). After 90 min the reaction mixture was diluted with ethyl acetate (40 mL), washed with 10% sodium thiosulphate solution (30 mL), saturated sodium bicarbonate solution (40 mL), and brine (40 mL). The combined aqueous layers were extracted with ethyl acetate (50 mL) and the combined organic layers were dried over sodium sulphate and concentrated under reduced pressure.

Workup

  1. washwashed with 10% sodium thiosulphate solution (30 mL), saturated sodium bicarbonate solution (40 mL), and brine (40 mL)
  2. extractionThe combined aqueous layers were extracted with ethyl acetate (50 mL)
  3. dry with materialthe combined organic layers were dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31d6d84e7af943bd8b0f60b0668c3388
Source dataset
uspto-grants-2015_04
Patent number
US09017645B2

Reaction notes

Loading…