1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Cbz-Asp(OBut)-Gly-OBn

HRID 964491

Reaktionsgleichung

Reaktionsgleichung von HRID 964491
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].Cl.[NH2:25][CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>ClCl.C(Cl)Cl>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([NH:25][CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])=[O:13])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1110824-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 11701227Benzyl 2-aminoacetate hydrochloride

Produkt 1

HCID 14375963Cbz-Asp(OBut)-Gly-OBnAusbeute 108,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 24526ChlorineLösungsmittel

Versuchsvorschrift

A mixture of Cbz-Asp(OBut)-OH (3590 mg, 11.1 mmol), HCl+H-Gly-OBn (3360 mg, 16.6 mmol), EDCI (3180 mg, 16.6 mmol), HOBt (2250 mg, 16.6 mmol) and DIEA (2900 mg, 16.6 mmol) in dry CH2 Cl2 (50 mL) was stirred at r.t. for six hours. The reaction mixture was added CH2Cl2 (150 mL) and washed with 1N HCl (200 mL), saturated NaHCO3 aq. (200 mL) and brine (200 mL). The organic layer was passed through an inch of SiO2 layer and the SiO2 was washed with 1/9=AcOEt/CH2Cl2 (200 mL). The eluent was evaporated in vacuo to give clear oil (5690 mg, 100%): 1H NMR (300 MHz, CDCl3) δ 7.368 (s, 10H), 7.082 (t, 1H), 6.013 (d, J=7.8 Hz, 1H), 5.164 (s, 2H), 5.126 (s, 2H), 4.592 (d, J=6.6 Hz, 1H), 4.072 (d, J=5.7 Hz, 2H), 2.891 (dd, J=18.2, 4.5 Hz, 1H), 2.641 (dd, J=17.1, 6.3 Hz, 1H), 1.423 (s, 9H); 13C NMR (300 MHz, CDCl3) δ 171.0, 170.9, 169.3, 136.1, 135.2, 129.7, 128.6 (2C), 128.4, 128.3, 128.2, 81.9, 67.3, 67.2, 51.1, 41.5, 37.3, 28.0.

Aufarbeitung

  1. washwashed with 1N HCl (200 mL), saturated NaHCO3 aq. (200 mL) and brine (200 mL)
  2. washthe SiO2 was washed with 1/9=AcOEt/CH2Cl2 (200 mL)
  3. customThe eluent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-874846bbe82a4e449dc38c8d22cfa6f1
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05770380

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