Methanol → methyl N-(tert-butoxycarbonyl)glycylglycinate

HRID 1863466Notes

Reaction equation

HRID 1863466 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].CO.C(N(CC)CC)C.ClC1C=C(Cl)C(Cl)=CC=1[O:26][C:27](=O)[CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>CN(C)C=O>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][C:27](=[O:26])[CH2:28][NH:29][C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 12799284t-Butoxycarbonylglycine-2,4,5-Trichlorophenyl Ester

Product 1

HCID 637608methyl N-(tert-butoxycarbonyl)glycylglycinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Prepare a solution of 1.98 g. of glycine methyl ester hydrochloride in dimethylformamide containing 8 ml. of methanol and 1.42 g. of triethylamine. Cool and stir the solution while adding 5.0 g. of t-butoxycarbonylglycine-2,4,5-trichlorophenyl ester in 25 ml. of dimethylformamide. Stir the reaction mixture overnight, filter and evaporate the filtrate to dryness under reduced pressure. Chromatograph the residue on 150 g. of silica gel and collect the desired product which is eluted by an ethyl acetate:chloroform (1:9) mixture. Evaporate the eluate to dryness and crystallize from hexane to obtain the title product (m.p. 132°-135° C.).

Workup

  1. customPrepare a solution of 1.98 g
  2. temperatureCool
  3. additionwhile adding 5.0 g
  4. stirringStir the reaction mixture overnight
  5. filtrationfilter
  6. customevaporate the filtrate to dryness under reduced pressure
  7. customof silica gel and collect the desired product which
  8. washis eluted by an ethyl acetate:chloroform (1:9) mixture
  9. customEvaporate the eluate to dryness
  10. customcrystallize from hexane

Sources & evidence

ORD record
ord-442fb92c95e24a1fa5e17d9ac1377c25
Source dataset
uspto-grants-1979_09
Patent number
US04169141

Reaction notes

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