1,2-Dichloroethane → HCID 15384663, Verbindung

HRID 2237370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2237370
C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[C:18]([O:22][C:23]([NH:25][C@@H:26]([C:31]([OH:33])=O)[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:24])([CH3:21])([CH3:20])[CH3:19].C(Cl)CCl.Cl.[CH2:39]([O:46][C:47](=[O:54])[C@H:48]([CH2:50][CH:51]([CH3:53])[CH3:52])[NH2:49])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>ClCCl>[CH2:39]([O:46][C:47](=[O:54])[C@H:48]([CH2:50][CH:51]([CH3:52])[CH3:53])[NH:49][C:31](=[O:33])[C@@H:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[NH:25][C:23]([O:22][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:24])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-Methylmorpholine2×HCID 757711-HydroxybenzotriazoleHCID 637604tert-Butoxycarbonyl-D-leucineHCID 12928659Benzyl L-leucinate--hydrogen chloride (1/1)

Produkt 1

HCID 15384663HCID 15384663, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

HOBt (4 equivalents, 540 mg, 4 mmol), N-methylmorpholine (3 equivalents, 3 mmol), N-tert-butoxycarbonyl-D-leucine (1.0 equivalent, 230 mg, 1 mmol; Bachem), EDC (2 equivalents, 380 mg, 2 mmol) and again N-methylmorpholine (2 equivalents, 2 mmol) are added successively at −10° C. to a solution of L-leucine benzyl ester hydrochloride (1.1 equivalents, 300 mg, 1.1 mmol; cf. T. Wakamiya, M. Kamata, S. Kusumoto, H. Kobayashi, Y. Sai, et al., Bull. Chem. Soc. Jpn., 1998, 71, 699-710) in dichloromethane p.a. (30 ml). The reaction mixture warms slowly (about 12 h) to RT, whereby complete conversion of the amine component is observed by means of HPLC. The reaction mixture is concentrated in vacuo, taken up in acetonitrile and purified by means of preparative HPLC (Method 13). 362 mg (80% of theory) of the title compound are obtained.

Aufarbeitung

  1. customThe reaction mixture warms slowly (about 12 h)
  2. customto RT
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. custompurified by means of preparative HPLC (Method 13)

Quellen und Nachweise

ORD-Eintrag
ord-636ecc3c58c64a02967925d031894330
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718611B2

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