N-Hydroxysuccinimide → L-Valine, N-((phenylmethoxy)carbonyl)-, 2,5-dioxo-1-pyrrolidinyl ester

HRID 1379389

Reaktionsgleichung

Reaktionsgleichung von HRID 1379389
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].O[N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[C:1]([NH:11][C@H:12]([C:16]([O:18][N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26])=[O:17])[CH:13]([CH3:14])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Komponenten

5

Edukt 3

HCID 80170N-HydroxysuccinimideHCID 726987N-Carbobenzoxy-L-valineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 853556L-Valine, N-((phenylmethoxy)carbonyl)-, 2,5-dioxo-1-pyrrolidinyl esterAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of 3.40 g (13.5 mmol) of Cbz-valine and 1.56 g (13.5 mmol) of N-hydroxysuccinimide in 200 ml of dichloromethane was treated with 2.86 g (14.9 mmol) of N-ethyl-N'-(dimethylaminopropyl) carbodiimide hydrochloride and stirred at ambient temperature for 4 h. The resulting solution was washed sequentially with 10% citric acid, aqueous NaHCO3, and water; dried over Na2SO4, and concentrated in vacuo to provide 4.00 g (85%) of the desired compound.

Aufarbeitung

  1. washThe resulting solution was washed sequentially with 10% citric acid, aqueous NaHCO3, and water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-387d33c3be4a4181918d183819916a5d
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05670675

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