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

HRID 1994430Notes

Reaction equation

HRID 1994430 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 85990941Methyl 2-benzyloxycarbonylamino-2-methyl-3-oxopropionateYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-2ce7eb1272fa44de9d3d6a3adee6ecee
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

Loading…