Water → 3-(2-Methylsulfanyl-pyrimidin-4-yl)-3-oxo-propionic acid tert-butyl ester

HRID 1455256노트

반응식

HRID 1455256 반응식
[C:1]([O:5][C:6](=[O:18])[CH2:7][CH:8]([OH:17])[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([S:15][CH3:16])[N:10]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:18])[CH2:7][C:8]([C:9]1[CH:14]=[CH:13][N:12]=[C:11]([S:15][CH3:16])[N:10]=1)=[O:17])([CH3:3])([CH3:4])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 159087TriacetoxyperiodinaneHCID 574380943-Hydroxy-3-(2-methylsulfanyl-pyrimidin-4-yl)-propionic acid tert-butyl ester

생성물 1

HCID 574380693-(2-Methylsulfanyl-pyrimidin-4-yl)-3-oxo-propionic acid tert-butyl ester수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-hydroxy-3-(2-methylsulfanyl-pyrimidin-4-yl)-propionic acid tert-butyl ester, 18, (5.6 g, 20.9 mmol) in CH2Cl2 is added Dess-Martin periodinane (10.7 g, 25.1 mmol) followed by H2O (0.5 mL, 25.1 mmol). After stirring 1 h at room temperature, the solution is poured into aqueous saturated Na2S2O4. The aqueous phase is extracted with CH2Cl2, then EtOAc. The combined organic phases are dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified over silica (10% EtOAc/hexanes) to afford 5.6 g (95% yield) of the desired product. 1H NMR (300 MHz, CDCl3) (observed 3:1 mixture of enol:keto tautomers) enol tautomer: δ 12.34 (s, OH), 8.67 (d, J=5.1 Hz, 1H), 7.48 (d, J=5.1 Hz, 1H), 6.35 (s, 1H), 2.62 (s, 3H), 1.57 (s, 9H); ESI+ MS: m/z (rel intensity) 269.1 (30, M++H).

후처리

  1. extractionThe aqueous phase is extracted with CH2Cl2
  2. dry with materialThe combined organic phases are dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue is purified over silica (10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-b27ff14e886340019bf17652d54723d5
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482356B2

반응 노트

불러오는 중…