Formaldehyde → HCID 12084907, compound

HRID 1795488Notes

Reaction equation

HRID 1795488 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]([OH:16])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]=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]([CH3:13])[C:14](=[O:16])[O:15][CH2:17]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 70832N-Cbz-d-alanine

Product 1

HCID 12084907HCID 12084907, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

In toluene (190 mL) were suspended benzyloxycarbonyl-D-alanine (19.3 g), paraformaldehyde (6.56 g) and p-toluenesulfonic acid monohydrate (0.17 g), and the mixture was heated at reflux while removing water produced. At the end of the reaction, the mixture was cooled to room temperature, and 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. The precipitated crystals were filtered to give the title compound (17.4 g) as white crystals in a yield of 85%.

Workup

  1. temperaturethe mixture 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
  9. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-3087bb51b9bb405ebca21558fc13ced2
Source dataset
uspto-grants-2006_04
Patent number
US07026515B2

Reaction notes

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