Trimethyl orthoformate → HCID 56611851, compound

HRID 1731970Notes

Reaction equation

HRID 1731970 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12](C=O)[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]([O:23][CH3:24])([O:21][CH3:22])OC>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:24][O:23][CH:18]([O:21][CH3:22])[C@H:12]([CH:13]([CH3:15])[CH3:14])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

5

Reactant 2

HCID 9005Trimethyl orthoformateHCID 11009915benzyl [(1S)-1-formyl-2-methylpropyl]carbamate

Product 1

HCID 56611851HCID 56611851, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Procedure

22.8 g (0.097 mol) of N-benzyloxycarbonyl-L-valinal were dissolved in 55 ml of dry methanol. The solution was treated with 10.8 g (0.102 mol) of trimethyl orthoformate and 0.3 g of toluene-4-sulphonic acid and the mixture was left to stand at room temperature for 16 hours. The solvents were removed by evaporation, the residue was dissolved in 150 ml of ethyl acetate and the solution was washed with 5% sodium bicarbonate solution and then with brine. After drying over magnesium sulphate and filtration, the solvent was removed by evaporation to yield 24.5 g (90%) of N-benzyloxycarbonyl-L-valinal dimethyl acetal as an oil; Rf-value [hexane/ethyl acetate (2:1)]: 0.69.

Workup

  1. waitthe mixture was left
  2. customThe solvents were removed by evaporation
  3. dissolutionthe residue was dissolved in 150 ml of ethyl acetate
  4. washthe solution was washed with 5% sodium bicarbonate solution
  5. dry with materialAfter drying over magnesium sulphate and filtration
  6. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-b70e3b194f994004b7d2ae1430ba74b4
Source dataset
uspto-grants-1986_11
Patent number
US04623639

Reaction notes

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