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

HRID 591270Notes

Reaction equation

HRID 591270 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.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>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

6

Reactant 3

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 11054918(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

Product 1

HCID 10901762tert-Butyl (S)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoateYield 99.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.10 g (4.0 mmol) tert-butyl N-(tert-butoxycarbonyl)-L-homoserinate (prepared according to J. Org. Chem. 1988, 53, 1900-1903) in dichloromethane (50 mL) was added pyridine (0.97 mL, 12.0 mmol), followed by 2.55 g Dess Martin periodinane (6.0 mmol), at room temperature. The mixture was stirred 90 min at room temperature prior to being diluted with ethyl acetate (40 mL). The mixture was washed with 10% aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate and brine. The organic layer was dried over sodium sulfate and then evaporated. The crude product (1.09 g, quantitative yield) was used immediately without further purification.

Workup

  1. washThe mixture was washed with 10% aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-27212c75d7a44312ab293cd2fdf0abdc
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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