1-Hydroxybenzotriazole → N-tert-Butoxycarbonyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide

HRID 2185404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185404
ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]([NH:33][C:34](=[O:48])[C@@H:35]2[CH2:39][C@@H:38]([NH2:40])[CH2:37][N:36]2[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH:24]=1.[OH:49][C@H:50]([CH2:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:51](O)=[O:52]>ClCCl.C(Cl)(Cl)Cl>[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]([NH:33][C:34](=[O:48])[C@@H:35]2[CH2:39][C@@H:38]([NH:40][C:51](=[O:52])[C@H:50]([OH:49])[CH2:54][CH2:55][C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[CH2:37][N:36]2[C:41]([O:43][C:44]([CH3:45])([CH3:47])[CH3:46])=[O:42])[CH:24]=1

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2759328(R)-2-Hydroxy-4-phenylbutyric acidHCID 70173042trans-4-Amino-N-tert-Butoxycarbonyl-L-Proline 3-Quinolylamide

Produkt 1

HCID 70173053N-tert-Butoxycarbonyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-QuinolylamideAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Hydroxybenzotriazole (147 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (766 mg) were added to a stirred solution of trans-4-amino-N-tert-butoxycarbonyl-L-proline 3-quinolylamide(E, 1.30 g) and (R)-2-hydroxy-4-phenylbutanoic acid (F, 720 mg) in dichloromethane (40 mL) at 0° C. The mixture was stirred at room temperature overnight. The reaction mixture was diluted with chloroform and washed with saturated sodium hydrogen carbonate and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=100:1, v/v) to give the title compound (1.85 g) as a colorless foam: 1H NMR (400 MHz, CDCl3) δ 1.45 (m, 9H), 1.70 (m, 2H), 1.94 (m, 1H), 2.15 (m, 1H), 2.75 (m, 2H), 3.29 (m, 1H), 3.80 (m, 1H), 4.11 (m, 1H), 4.53 (m, 1H), 4.60 (m, 1H), 6.76 (m, 1H), 7.15-7.26 (m, 5H), 7.48 (m, 1H), 7.57 (m, 1H), 7.73 (m, 1H), 7.95 (d, J=16.8 Hz, 1H), 8.68 (s, 1H), and 8.69 (s,1H).

Aufarbeitung

  1. washwashed with saturated sodium hydrogen carbonate and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (chloroform

Quellen und Nachweise

ORD-Eintrag
ord-31a064d2fdbb470389af30b74b953efe
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399629B1

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