Formaldehyde → HCID 14554283, compound

HRID 653855Notes

Reaction equation

HRID 653855 reaction equation
F[C:2](F)(F)C(O)=O.N[C@@H:9]([C:12]([NH2:14])=[O:13])[CH2:10][OH:11].C(=O)(O)[O-].[Na+].C=O.[C:22]([BH3-])#[N:23].[Na+]>O.C(#N)C>[CH3:2][N:23]([CH3:22])[C@H:9]([CH2:10][OH:11])[C:12]([NH2:14])=[O:13]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 86745965HCID 86745965, compound

Product 1

HCID 14554283HCID 14554283, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
-5 °C

Procedure

D-serine amide trifluoroacetate (9.0 g) was dissolved in water (12.6 ml). Under ice cooling, sodium bicarbonate (3.47 g) was added, followed by stirring for 10 minutes. The resulting mixture was added with acetonitrile (66.6 ml) to form a suspension. Under cooling at -5° C., were added a 37% aqueous solution (7.37 g) of formaldehyde and sodium cyanoborohydride (1.74 g), followed by stirring for 1 hour. An insoluble matter deposited was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a column packed with alumina (450 g), thereby obtaining the target product (3.4 g).

Workup

  1. customto form a suspension
  2. stirringby stirring for 1 hour
  3. filtrationAn insoluble matter deposited was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by chromatography on a column

Sources & evidence

ORD record
ord-727c43b38184475a920e512d0f8ac94a
Source dataset
uspto-grants-1992_07
Patent number
US05128465

Reaction notes

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