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

HRID 1758837노트

반응식

HRID 1758837 반응식
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]

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 2733413Proline benzyl ester hydrochlorideHCID 54011285HCID 54011285, 화합물HCID 54407250HCID 54407250, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매2회HCID 8471Triethylamine용매

실험 절차

Dissolve 0.75 g of N-(1-carbobenzoxyethyl)-L-alanine in pyridine and add 7.5 ml of 1 M 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.

후처리

  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

출처 및 근거

ORD 기록
ord-82f6eee09e4f489f9c5ad9d8d6f68716
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04374829

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