Chloroform → Ethyl N-(1-((benzyloxy)carbonyl)-L-prolyl)-L-leucinate

HRID 1733652Notes

Reaction equation

HRID 1733652 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:20]([O:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH2:25])[CH3:21].C(Cl)(Cl)Cl.CS(ON=C(C#N)C(OCC)=O)(=O)=O>C(N(CC)CC)C>[CH2:20]([O:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH:25][C:13](=[O:15])[C@@H:12]1[CH2:16][CH2:17][CH2:18][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:21]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 101987Benzyloxycarbonyl-L-prolineHCID 11658447L-Leucine, ethyl ester, hydrochloride (1:1)HCID 54531055Ethyl cyano{[(methanesulfonyl)oxy]imino}acetate

Product 1

HCID 6453075Ethyl N-(1-((benzyloxy)carbonyl)-L-prolyl)-L-leucinateYield 40.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

N-Benzyloxycarbonyl-L-proline (1.25 g) and L-leucine ethyl ester hydrochloride (1.0 g) are suspended into chloroform (10 ml), and therein is dissolved triethylamine (1.40 ml). To the solution is added ethyl 2-methanesulfonyloxyimino-2-cyanoacetate (1.1 g) and the mixture is stirred at room temperature for 16 hours. After reaction, the reaction mixture is extracted with ethyl acetate. The extract is washed with water, 1 N aqueous sodium hydrogen carbonate, water, 1 N hydrochloric acid and water in order and then dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off and the resulting residue is crystallized from petroleum ether to give N-(N-benzyloxycarbonyl-L-prolyl)-L-leucine ethyl ester (0.8 g), melting point: 65°-67° C.

Workup

  1. customAfter reaction
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. washThe extract is washed with water, 1 N aqueous sodium hydrogen carbonate, water, 1 N hydrochloric acid and water in order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter drying
  6. distillationthe solvent is distilled off
  7. customthe resulting residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-8efbbd2f237244b7b894d13b45c3f98b
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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