Diethyl Ether → HCID 86678816, compound

HRID 1649890Notes

Reaction equation

HRID 1649890 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:16])[C:10](=[O:15])[C@@H:11]([CH2:13][OH:14])[NH2:12].[OH-].[Na+].C(OCC)C>CN(C)C=O.CO>[CH3:8][N:9]([CH3:16])[C:10](=[O:15])[C@@H:11]([CH2:13][OH:14])[NH2:12]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 88494753HCID 88494753, compound

Product 1

HCID 86678816HCID 86678816, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

The compound (1.00 g) prepared in Experiment 4 was dissolved in dimethylformamide (2 ml). A solution of N,N-dimethyl-D-serinamide was prepared by dissolving N,N-dimethyl-D-serinamide trifluoroacetate (590 mg) in methanol (5 ml), adding 1N-aqueous sodium hydroxide solution (2.4 ml) thereto, followed by distilling off the solvent under reduced pressure, and extracting the residue with acetonitrile (2 ml). The N,N-dimethyl-D-serinamide solution was added to the solution of the compound prepared in Experiment 4 in dimethylformamide under ice-cooling. The resulting solution was stirred for 30 minutes. The reaction solution was added to ethyl ether, and the resulting precipitates were collected by filtration to obtain yellow powder (1.1 g).

Workup

  1. distillationby distilling off the solvent under reduced pressure
  2. extractionextracting the residue with acetonitrile (2 ml)
  3. additionThe N,N-dimethyl-D-serinamide solution was added to the solution of the compound
  4. customprepared in Experiment 4 in dimethylformamide under ice-
  5. temperaturecooling
  6. customthe resulting precipitates
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f9fa0c1d33b64fcd9cdbae2c8c549f21
Source dataset
uspto-grants-1990_05
Patent number
US04921850

Reaction notes

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