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

HRID 1758837ノート

反応式

HRID 1758837 の反応式
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]

参加物

7

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 2733413Proline benzyl ester hydrochlorideHCID 54011285HCID 54011285、化合物HCID 54407250HCID 54407250、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-82f6eee09e4f489f9c5ad9d8d6f68716
出典データセット
uspto-grants-1983_02
特許番号
US04374829

反応ノート

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