Formaldehyde → HCID 11807514, compound

HRID 479871Notes

Reaction equation

HRID 479871 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]=O.O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:8][C:9]([N:11]1[C@@H:12]([CH:13]([CH3:15])[CH3:14])[C:16](=[O:18])[O:17][CH2:19]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 11807514HCID 11807514, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-valine (25.1 g, 0.1 mol) in toluene (500 ml) was added paraformaldehyde (4.0 g) and p-toluenesulfonic acid monohydrate (1.0 g), and the mixture was refluxed for 30 minutes, during which the generated water was removed by a Dean-stalk apparatus. The reaction solution was washed successively with 5% aqueous sodium hydrogen carbonate solution and saturate brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from toluene to give the desired compound (25.0 g, yield: 95%).

Workup

  1. customwas removed by a Dean-stalk apparatus
  2. washThe reaction solution was washed successively with 5% aqueous sodium hydrogen carbonate solution
  3. concentrationsaturate brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-acf5c1d51b8b463c8101ee6172269065
Source dataset
uspto-grants-2003_11
Patent number
US06646150B1

Reaction notes

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