Triethylamine → 6-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid methyl ester

HRID 249628

Reaktionsgleichung

Reaktionsgleichung von HRID 249628
Cl.[CH3:2][O:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH2:10].[C:12]([NH:22][CH2:23][CH2:24][C:25](O)=[O:26])([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].C(N=C=NCCCN(C)C)C.CCN(CC)CC>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:25](=[O:26])[CH2:24][CH2:23][NH:22][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 11499324Methyl 6-aminohexanoate hydrochloride

Produkt 1

HCID 692961146-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid methyl esterAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound 35 was prepared using General Procedure B with 6-aminohexanoic acid methyl ester hydrochloride salt (3.0 g, 16.5 mmol), N-Cbz-β-alanine (3.68 g, 16.5 mmol), 1-hydrobenzotriazole (HOBt) (2.68 g, 19.8 mmol), 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide (EDC) (3.80 g, 19.8 mmol) and Et3N (5.52 mL, 39.6 mmol) in CH2Cl2, (100 mL). Recrystallization of the crude product from a mixture of MeOH and H2O (10:1 ratio) afforded 5.28 g (91%) of the desired product (35) as a white solid. 1H NMR (CDCl3): 7.32 (m, 5H, ArH), 5.82 (s, 1H, NH), 5.54 (s, 1H, NH), 5.07 (s, 2H, OCH2Ar), 3.64 (s, 3H, OCH3), 3.45 (dt, J=6.1, 12.0 Hz, 2H, CH2NHCO), 3.21 (dt, J=6.4, 12.8 Hz, 2H, CH2NHCO), 2.38 (dt, J=6.1, 6.8 Hz, 2H, CH2CO), 2.29 (t, J=7.2 Hz, 2H, CH2CO), 1.61 (m, 2H, CH2), 1.48 (m, 2H, CH2), 1.33 (m, 2H, CH2).

Aufarbeitung

  1. customThe compound 35 was prepared
  2. customRecrystallization of the crude product
  3. additionfrom a mixture of MeOH and H2O (10:1 ratio)

Quellen und Nachweise

ORD-Eintrag
ord-84dd51e6c2ab403abd8a19fbc991fd46
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07862807B2

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