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

HRID 1455256ノート

反応式

HRID 1455256 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b27ff14e886340019bf17652d54723d5
出典データセット
uspto-grants-2009_01
特許番号
US07482356B2

反応ノート

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