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

HRID 591270노트

반응식

HRID 591270 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-27212c75d7a44312ab293cd2fdf0abdc
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238631B2

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