Formaldehyde → HCID 11807514, compound

HRID 1795484Notes

Reaction equation

HRID 1795484 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>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

5

Reactant 2

HCID 712FormaldehydeHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 11807514HCID 11807514, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

In toluene (250 mL) were suspended benzyloxycarbonyl-L-valine (25.1 g), paraformaldehyde (6.70 g) and p-toluenesulfonic acid monohydrate (0.19 g), and the suspension was heated at reflux while removing water produced. At the end of the reaction, the mixture was cooled to room temperature, washed with saturated aqueous sodium hydrogen carbonate solution and saturated saline. The toluene solution was dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give the title compound (23.7 g) as colorless transparent syrup in an yield of 90%.

Workup

  1. temperaturethe suspension was heated
  2. temperatureat reflux
  3. customwhile removing water
  4. customproduced
  5. customAt the end of the reaction
  6. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated saline
  7. dry with materialThe toluene solution was dried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-043834453f364ed6852bca6791bb8319
Source dataset
uspto-grants-2006_04
Patent number
US07026515B2

Reaction notes

Loading…