Formaldehyde → HCID 58691300, compound

HRID 602323Notes

Reaction equation

HRID 602323 reaction equation
[CH2:1]=O.[NH2:3][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:5][OH:6].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1>[OH-].[Na+]>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([N:3]2[C@@H:4]([C:7]([OH:9])=[O:8])[CH2:5][O:6][CH2:1]2)=[O:19])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 76934-Chlorophenyl IsocyanateHCID 71077D-Serine

Product 1

HCID 58691300HCID 58691300, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

2.1 1.49 ml (20.0 mmol) of 37% aqueous formaldehyde solution are added to a solution of 2.10 g (20.0 mmol) of D-serine in 10 ml of 1N aqueous sodium hydroxide solution. The resultant solution is left at 5° C. for 18 hours. The solution is heated to 80° C., 6.14 g (40 mmol) of 4-chlorophenyl isocyanate are added, and the mixture is stirred at this temperature for one hour. The mixture is allowed to cool, and the precipitate formed is filtered off. The filtrate is acidified using 1N HCl, and the precipitate formed is filtered off and dried, giving (R)-3-(4-chlorophenylcarbamoyl)oxazolidine-4-carboxylic acid as a colourless solid; ESI 271.

Workup

  1. temperatureto cool
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. customdried

Sources & evidence

ORD record
ord-c8dddf6e013343ad97340120c5e82274
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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