4-Methylmorpholine → Benzyl (tert-butoxycarbonyl)glycylglycinate

HRID 1759185Notes

Reaction equation

HRID 1759185 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:23])[CH2:21][NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN1CCOCC1.ClC1C=C(Cl)C(Cl)=CC=1[O:40][C:41](=O)[CH2:42][NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45]>CN(C)C=O>[CH2:12]([O:19][C:20](=[O:23])[CH2:21][NH:22][C:41](=[O:40])[CH2:42][NH:43][C:44]([O:46][C:47]([CH3:49])([CH3:48])[CH3:50])=[O:45])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 12799284t-Butoxycarbonylglycine-2,4,5-Trichlorophenyl Ester

Product 1

HCID 3244524Benzyl (tert-butoxycarbonyl)glycylglycinateYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.2 g (42 mmoles) of glycine benzyl ester p-toluenesulfonate are dissolved in 100 ml of dimethyl formamide, 4.6 ml (42 mmoles) of N-methylmorpholine and 14.2 g (40 mmoles) of tert.-butoxycarbonyl-glycine 2,4,5-trichlorophenyl ester are added, and the mixture is stirred at room temperature overnight. The reaction mixture is evaporated, and the residue is dissolved in a mixture of 150 ml of ethyl acetate and 50 ml of water. The ethyl acetate phase is washed twice with 30 ml of ice-cooled 1 n aqueous hydrochloric acid, each, and then with water, dried over sodium sulfate and evaporated. The residue is triturated with a 1:1 mixture of diisopropyl ether and petroleum ether, filtered, the solid is washed with the same solvent mixture and dried in a desiccator. 11.0 g (82.8%) of tert.-butoxycarbonyl-glycyl-glycine benzyl ester are obtained; m.p.: 83° C., Rf14 =0.1-0.2.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in a mixture of 150 ml of ethyl acetate and 50 ml of water
  3. washThe ethyl acetate phase is washed twice with 30 ml of ice-
  4. temperaturecooled 1 n aqueous hydrochloric acid
  5. dry with materialeach, and then with water, dried over sodium sulfate
  6. customevaporated
  7. customThe residue is triturated with a 1:1 mixture of diisopropyl ether and petroleum ether
  8. filtrationfiltered
  9. washthe solid is washed with the same solvent mixture
  10. customdried in a desiccator

Sources & evidence

ORD record
ord-fe4b1dcd72074e8ca6a2f50c3bf96258
Source dataset
uspto-grants-1982_07
Patent number
US04339440

Reaction notes

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