Formaldehyde → HCID 12084899, compound

HRID 1795483Notes

Reaction equation

HRID 1795483 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]=O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([O:5][C:6]([N:8]1[C@@H:9]([CH3:10])[C:11](=[O:13])[O:12][CH2:14]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 12084899HCID 12084899, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

In toluene (250 mL) were suspended tert-butoxycarbonyl-L-alanine (18.9 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, and the crystals obtained were filtered to give the title compound (14.2 g) white crystals in a yield of 71%.

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
  9. customthe crystals obtained
  10. filtrationwere filtered

Sources & evidence

ORD record
ord-7bee979f66844bcc866467f5b515b3f0
Source dataset
uspto-grants-2006_04
Patent number
US07026515B2

Reaction notes

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