Formaldehyde → HCID 22646456, compound

HRID 393983Notes

Reaction equation

HRID 393983 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([OH:13])[C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[OH-].[Na+].C=O.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[C:23](Cl)=[O:24].[C:33](=O)(O)[O-].[Na+]>CC(C)=O>[C:4]1([CH:7]2[O:13][CH2:33][N:12]([C:23](=[O:24])[C:22]3[CH:21]=[C:20]([O:19][CH3:18])[C:28]([O:29][CH3:30])=[C:27]([O:31][CH3:32])[CH:26]=3)[CH:8]2[C:9]([OH:11])=[O:10])[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 111178L-threo-3-PhenylserineHCID 516892Sodium Bicarbonate

Product 1

HCID 22646456HCID 22646456, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

DL-threo-3-Phenylserine hydrate (5.00 g, 27.6 mmol) and 2N NaOH (13.8 mL, 27.6 mmol) are combined and cooled in an ice-bath. Formaldehyde (2.24 g of a 37% aqueous solution) is added and the reaction mixture is stirred at 0° C. for 21 hours. A solution of 3,4,5-trimethoxybenzoyl chloride (6.36 g, 27.6 mmol) in acetone (20 mL) is added slowly using solid sodium bicarbonate to maintain the pH>7. After stirring for 1 hour the reaction mixture is poured onto water and extracted with ethyl acetate (3×50 mL). The aqueous solution is cooled in an ice-bath, the pH is adjusted to 1 with 1N HCl and the mixture is extracted with methylene chloride (3×100 mL). The combined methylene chloride extracts are washed with water, dried over magnesium sulfate, filtered and concentrated at reduced pressure to afford the desired product as a white solid. CIMS: MH+ 388

Workup

  1. temperaturecooled in an ice-bath
  2. temperatureto maintain the pH>7
  3. stirringAfter stirring for 1 hour the reaction mixture
  4. additionis poured onto water
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. temperatureThe aqueous solution is cooled in an ice-bath
  7. extractionthe mixture is extracted with methylene chloride (3×100 mL)
  8. washThe combined methylene chloride extracts are washed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-4541d8805f374c589d24338a3cbd48e3
Source dataset
uspto-grants-2004_10
Patent number
US06809093B2

Reaction notes

Loading…