Methyl formate → HCID 70395751, compound

HRID 1639006Notes

Reaction equation

HRID 1639006 reaction equation
[C:1]([N:11]([CH2:13][C:14](O)=[O:15])[CH3:12])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:17]([O:19][CH3:20])=[O:18].[H-].[Na+]>CN(C=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[C:1]([N:11]([CH3:12])[C:13](=[CH:14][OH:15])[C:17]([O:19][CH3:20])=[O:18])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7865Methyl formate2×HCID 24758Sodium hydrideHCID 13605080HCID 13605080, compound

Product 1

HCID 70395751HCID 70395751, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

A solution of the methyl ester of E-N-cinnamoylsarcosine (2.03 g) and methyl formate (ca. 11 ml) in dry DMF (15 ml) was added to a stirred suspension of sodium hydride (0.42 g) in dry DMF (20 ml). Only gentle effervescence was observed at first, but after 40 minutes brisk effervescence began [further methyl formate (3 ml) added], subsiding after about 15 minutes and continuing gently until the mixture was carefully diluted with aqueous sodium carbonate after 7.5 hours. The mixture was extracted with ether, and the extracts were washed with aqueous sodium carbonate then water, dried and concentrated under reduced pressure to give recovered E-N-cinnamoylsarcosine methyl ester (0.975 g). The original basic aqueous layer was acidified with concentrated hydrochloric acid and extracted with ether. The extracts were washed with water, dried and concentrated under reduced pressure to give methyl N-cinnamoyl-N-methyl-2-amino-3-hydroxypropenoate (1.108 g, 49% yield, or 94% based on recovered starting material) as a pale red glass, used without further purification for the next step. The proton n.m.r. spectrum recorded using deuteriochloroform as solvent showed duplication of some signals (presumably due to restricted rotation about the amide bond). However, with deuterated dimethylsulphoxide as solvent, the following single set of signals was seen:

Workup

  1. customafter 40 minutes
  2. extractionThe mixture was extracted with ether
  3. washthe extracts were washed with aqueous sodium carbonate
  4. dry with materialwater, dried
  5. concentrationconcentrated under reduced pressure
  6. customto give
  7. customrecovered E-N-cinnamoylsarcosine methyl ester (0.975 g)
  8. extractionextracted with ether
  9. washThe extracts were washed with water
  10. customdried
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-396a823d038e4ea3b931e1014bbfea6c
Source dataset
uspto-grants-1989_11
Patent number
US04882341

Reaction notes

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