Dicyclohexylcarbodiimide → N-(1-Carboxyethyl)-L-alanyl-L-proline

HRID 2418411Notes

Reaction equation

HRID 2418411 reaction equation
C(C(N[C@H](C(O)=O)C)C)(OCC1C=CC=CC=1)=O.Cl.C(OC(=O)[C@@H]1CCCN1)C1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:50]([CH:60]([NH:62][C@H:63]([C:65]([N:67]1[CH2:74][CH2:73][CH2:72][C@H:68]1[C:69]([OH:71])=[O:70])=[O:66])[CH3:64])[CH3:61])([O:52]CC1C=CC=CC=1)=[O:51]>N1C=CC=CC=1.C(N(CC)CC)C>[C:50]([CH:60]([NH:62][C@H:63]([C:65]([N:67]1[CH2:74][CH2:73][CH2:72][C@H:68]1[C:69]([OH:71])=[O:70])=[O:66])[CH3:64])[CH3:61])([OH:52])=[O:51]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 2733413Proline benzyl ester hydrochlorideHCID 54011285HCID 54011285, compoundHCID 54407250HCID 54407250, compound

Product 1

HCID 53882949N-(1-Carboxyethyl)-L-alanyl-L-proline

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8471TriethylamineSolvent

Procedure

Dissolve 0.75 g of N-(1-carbobenzoxyethyl)-L-alanine in pyridine and add 7.5 ml of 1M triethylamine in pyridine. Cool, and add 1.09 g L-proline benzyl ester hydrochloride and 0.678 g dicyclohexylcarbodiimide. Store at 0° C. for 20 hours. Filter, then concentrate the reaction mixture in vacuo. Dissolve the residue in ethyl acetate and wash this solution with saturated K2CO3, then brine. Dry the organic phase, concentrate in vacuo, then chromatograph the residue on silica gel with ethyl acetate-hexane to isolate the diastereoisomeric mixture of N-(1-carbobenzoxyethyl)-L-alanyl-L-proline.

Workup

  1. temperatureCool
  2. filtrationFilter
  3. concentrationconcentrate the reaction mixture in vacuo
  4. dissolutionDissolve the residue in ethyl acetate
  5. washwash this solution with saturated K2CO3
  6. customDry the organic phase
  7. concentrationconcentrate in vacuo
  8. customchromatograph the residue on silica gel with ethyl acetate-hexane to isolate

Sources & evidence

ORD record
ord-ae4272277d824605abc03a06461be78b
Source dataset
uspto-grants-1984_09
Patent number
US04472380

Reaction notes

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