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Triethylamine → Boc-Leu-Leu-Lys(Z)-OBzl

HRID 1513530
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1513530
[NH2:1][C@H:2]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].Cl.CCN(CC)CC.[NH:36]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[C@H:37]([C:42]([NH:44][C@H:45]([C:50](O)=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH2:38][CH:39]([CH3:41])[CH3:40].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.C(O)(=O)C>[NH:36]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[C@H:37]([C:42]([NH:44][C@H:45]([C:50]([NH:1][C@H:2]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])=[O:51])[CH2:46][CH:47]([CH3:48])[CH3:49])=[O:43])[CH2:38][CH:39]([CH3:41])[CH3:40]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7019882(S)-2-((S)-2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanoic acidHCID 11750132L-Lysine, N6-((phenylmethoxy)carbonyl)-, phenylmethyl ester, hydrochloride (1:1)

Produkt 1

HCID 12020549
Boc-Leu-Leu-Lys(Z)-OBzl
Ausbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of H-Lys(Z)—OBzl.HCl (20.35 g, 50 mmol) in DMF (50.0 g) was treated with Et3N (5.26 g, 51 mmol) at 25 to 30° C. Boc-Leu-Leu-OH (17.57 g, 51 mmol) and HOBt (1.08 g, 8 mmol) were added followed by an additional portion of DMF (7.0 g). A solution of DCC (11.35 g, 55 mmol) in DMF (25.0 g) was added dropwise over a period of 30 min at 20° C. The reaction mixture was stirred for 4 h and the temperature was allowed to rise (to ca. 34° C.). Acetic acid (0.2 g) was added, the resulting suspension was filtered and the filter cake was rinsed with DMF (15.0 g). Acetone (126.0 g) was added to the filtrate, followed by two portions of H2O (66.5 g, 89.5 g-30 min apart). The resulting precipitate was filtered and the filter cake was washed with acetone (53.0 g) and H2O (212.0 g). The crude solid was triturated with a mixture of acetone (100 g) and H2O (400 g), filtered, washed with H2O and dried in vacuo at 40° C. to give Boc-Leu-Leu-Lys(Z)—OBzl (32.6 g, 93.4%).

Aufarbeitung

  1. custom(to ca. 34° C.)
  2. filtrationthe resulting suspension was filtered
  3. washthe filter cake was rinsed with DMF (15.0 g)
  4. additionAcetone (126.0 g) was added to the filtrate
  5. filtrationThe resulting precipitate was filtered
  6. washthe filter cake was washed with acetone (53.0 g) and H2O (212.0 g)
  7. customThe crude solid was triturated with a mixture of acetone (100 g) and H2O (400 g)
  8. filtrationfiltered
  9. washwashed with H2O
  10. customdried in vacuo at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-cf2584ec478c48229bb19d2aa2dfb6cd
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08217142B2

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