N-Ethylpiperidine → Benzyloxycarbonylglutaminyl-glycyl-glycine methyl ester

HRID 986351Notes

Reaction equation

HRID 986351 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[CH2:5][NH:6][C:7](=[O:10])[CH2:8][NH2:9].C(N1CCCCC1)C.ClC1C([O:27][C:28](=O)[C@H:29]([CH2:41][CH2:42][C:43](=[O:45])[NH2:44])[NH:30][C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])=C(Cl)C(Cl)=C(Cl)C=1Cl>CN(C)C=O.ClCCl>[CH3:2][O:3][C:4](=[O:11])[CH2:5][NH:6][C:7](=[O:10])[CH2:8][NH:9][C:28](=[O:27])[C@H:29]([CH2:41][CH2:42][C:43](=[O:45])[NH2:44])[NH:30][C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32]

Participants

5

Reactant 3

HCID 13007N-EthylpiperidineHCID 117402N2-Benzyl pentachlorophenyl N2-carboxy-L-(2-aminoglutaramate)HCID 13029724Methyl 2-(2-aminoacetamido)acetate hydrochloride

Product 1

HCID 14369391Benzyloxycarbonylglutaminyl-glycyl-glycine methyl ester

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A suspension of glycyl-glycine methyl ester hydrochloride (1.9 g; 10 mmoles) in a dimethylformamide-dichloromethane (1:2) mixture (30 ml) is admixed with N-ethylpiperidine (1.4 ml) and stirred for 2 hours at room temperature. After that benzyloxycarbonylglutamine pentachlorphenyl ester (5.3 g; 10 mmoles) is added and the reaction mixture is stirred at room temperature a further 4 hours. After 8 hours of standing, the precipitated crystalline product is separated and crystallized from methanol - dichloromethane. Yield 2.5 g (61%), m.p. 129°-134° C., after additional crystallization from methanol 132°-134° C. Rf 0.57/S1, 0.78/S2⟦alpha⟧sub.D20 -8.5° (c 0.2; 50% acetic acid). Composition: C18H24N4O7.1/2H2O.

Workup

  1. stirringthe reaction mixture is stirred at room temperature a further 4 hours
  2. waitAfter 8 hours of standing
  3. customthe precipitated crystalline product is separated
  4. customcrystallized from methanol - dichloromethane
  5. customYield 2.5 g (61%), m.p. 129°-134° C., after additional crystallization from methanol 132°-134° C
  6. customRf 0.57/S1, 0.78/S2⟦alpha⟧sub.D20 -8.5° (c 0.2; 50% acetic acid)

Sources & evidence

ORD record
ord-29c8b4a996c24fd987f7fa4d9d1a3c21
Source dataset
uspto-grants-1987_12
Patent number
US04711952

Reaction notes

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