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Triethylamine → Z-Asp(OtBu)-Val-OtBu

HRID 2371371
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2371371
C(N(CC)CC)C.[NH2:8][C@H:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:10]([CH3:12])[CH3:11].Cl.[NH:21]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C@H:22]([C:31](ON1C(=O)CCC1=O)=[O:32])[CH2:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]>CN(C)C=O>[NH:21]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C@H:22]([C:31]([NH:8][C@H:9]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:32])[CH2:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 11026196L-Aspartic acid, N-((phenylmethoxy)carbonyl)-, 4-(1,1-dimethylethyl) 1-(2,5-dioxo-1-pyrrolidinyl) esterHCID 12490702tert-butyl (2S)-2-amino-3-methylbutanoate hydrochloride

Produkt 1

HCID 70050186Z-Asp(OtBu)-Val-OtBuAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

1.68 ml (12.0 mmol) of triethylamine are added to a suspension containing 2.58 g (12.0 mmol) of H-Val-OtBu.HCl and 4.62 g (11.0 mmol) of Z-Asp(OtBu)-OSu in 25 ml of dimethylformamide (DMF). The reaction mixture is left to stand overnight, then evaporated under reduced pressure. The residue is mixed with 50 ml of ethyl acetate and the suspension obtained is successively washed with 25 ml of water, 3 times with 25 ml of 1 mol/liter hydrochloric acid each, 3 times with 25 ml of 5% aqueous sodium hydrogenocarbonate each and finally with 25 ml of water, dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain 4.3 g (81.7%) of oily Z-Asp(OtBu)-Val-OtBu protected dipeptide, Rf1 =0.85.

Aufarbeitung

  1. waitThe reaction mixture is left
  2. customevaporated under reduced pressure
  3. additionThe residue is mixed with 50 ml of ethyl acetate
  4. customthe suspension obtained
  5. washis successively washed with 25 ml of water, 3 times with 25 ml of 1 mol/liter hydrochloric acid each, 3 times with 25 ml of 5% aqueous sodium
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-80e1ff23442740fab22af43a8ce136fb
Quelldatensatz
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05093320

Notizen zur Reaktion

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