Diethyl Ether → Methyl 2-benzyloxycarbonylamino-2-methyl-3-oxopropionate

HRID 1994430ノート

反応式

HRID 1994430 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31]([NH:33][C:34]([CH3:41])([CH2:39][OH:40])[C:35]([O:37][CH3:38])=[O:36])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:23]([O:30][C:31]([NH:33][C:34]([CH3:41])([CH:39]=[O:40])[C:35]([O:37][CH3:38])=[O:36])=[O:32])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 14185548Methyl 2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-2-methylpropanoate

生成物 1

HCID 85990941Methyl 2-benzyloxycarbonylamino-2-methyl-3-oxopropionate収率 71.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 97.7 mg (0.23 mmol) of Dess Martin periodinane reagent (Aldrich) in 1 ml of DCM is slowly added dropwise to a solution of 56 mg (0.21 mmol) of methyl 2-benzyloxycarbonylamino-3-hydroxy-2-methylpropionate in 1 ml of DCM, and the mixture is left to stir at room temperature for 30 min. 5 ml of diethyl ether and a mixture of 4 ml of saturated NaHCO3 and 0.36 g of Na2S2O3.5H2O are then added to the solution. It is stirred for 15 min until the solid has dissolved, and then the ether phase is washed with saturated NaHCO3 and water, dried over MgSO4 and concentrated in vacuo. The crude product is purified by chromatography on 4 g of SiO2 with EtOAc/heptane (gradient 0-50%). 40 mg of the desired aldehyde are obtained.

後処理

  1. waitthe mixture is left
  2. additionare then added to the solution
  3. stirringIt is stirred for 15 min until the solid
  4. dissolutionhas dissolved
  5. washthe ether phase is washed with saturated NaHCO3 and water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by chromatography on 4 g of SiO2 with EtOAc/heptane (gradient 0-50%)

出典と根拠

ORDレコード
ord-2ce7eb1272fa44de9d3d6a3adee6ecee
出典データセット
uspto-grants-2010_01
特許番号
US07652007B2

反応ノート

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