Formic Acid → methyl N-(2,3-dihydro-3-methyl-1H-inden-1-yl)-N-formylglycine

HRID 5780Notes

Reaction equation

HRID 5780 reaction equation
[CH3:1][N:2]([CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]([CH3:16])[CH2:8]1)[CH2:3][C:4](O)=O.C(OC(=O)C)(=[O:19])C.[CH:24]([OH:26])=[O:25]>>[CH3:4][CH:3]([C:24]([OH:26])=[O:25])[N:2]([CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]([CH3:16])[CH2:8]1)[CH:1]=[O:19]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 67861921methyl N-(2,3-dihydro-3-methyl-1H-inden-1-yl)glycine

Product 1

HCID 19794121methyl N-(2,3-dihydro-3-methyl-1H-inden-1-yl)-N-formylglycineYield 78.7%

Procedure

A solution of 17 parts of methyl N-(2,3-dihydro-3-methyl-1H-inden-1-yl)glycine in 60 parts of formic acid and 20 parts of acetic acid anhydride is stirred overnight at room temperature. The reaction mixture is evaporated in vacuo and the residue is taken up in 1,1'-oxybisethane. The organic layer is washed with a sodium hydrogen carbonate solution and water dried, filtered and evaporated. The residue is crystallized from a mixture of 2,2'-oxybispropane and hexane. The product is filtered off and dried, yielding 15 parts (78.7%) of methyl N-(2,3-dihydro-3-methyl-1H-inden-1-yl)-N-formylglycine.

Workup

  1. customThe reaction mixture is evaporated in vacuo
  2. washThe organic layer is washed with a sodium hydrogen carbonate solution and water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is crystallized from a mixture of 2,2'-oxybispropane and hexane
  7. filtrationThe product is filtered off
  8. customdried

Sources & evidence

ORD record
ord-a873420835704421bdbe4d1c155cadc8
Source dataset
uspto-grants-1993_09
Patent number
US05246915

Reaction notes

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