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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 592508Erstellt: 26. Oktober 2026

1-Hydroxybenzotriazole → Fmoc-Tyr(tBu)-Lys(Z)-OMe

https://huagongshe.com/reaction/592508

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt1-HydroxybenzotriazoleHCID 75771—
EduktDiisopropylethylamineHCID 81531—
Edukt1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
Eduktmethyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoateHCID 6994982—
EduktFmoc-L-Tyr(tBu)-OHHCID 10895791—
LösungsmittelDichloromethaneHCID 6344—
ProduktFmoc-Tyr(tBu)-Lys(Z)-OMeHCID 13173455697,5%

Reaktionsschritte

To a solution of diisopropylethyl amine (1.19 mL, 3.43 mmol) in DCM (50 mL), was added Lys(Z)OMe (1.13 g, 3.43 mmol). To this solution was added FmocTyr(tBu)OH (1.50 g, 3.26 mmol), then HOBt (0.463 g, 3.43 mmol), and finally EDC.HCl (0.6571 g, 3.43 mmol). This solution was allowed to stir for 8 h at which time the organic solution was washed with 1N HCl (2×20 mL), then saturated NaHCO3 (2×20 mL), and finally H2O (2×20 mL). The organic layer was concentrated in vacuo to yield a white solid (2.34 g, 97.5% yield): 1H NMR (500 MHz, CDCl3) δ 7.77 (d, J=7.53, 2H), 7.55 (m, 2H), 7.40 (t, J=7.45, 2H), 7.38-7.29 (m, 7H), 7.08 (m, 2H), 6.88 (d, J=8.25, 2H), 6.43 (br s, 1H), 5.52 (br s, 1H), 5.15-5.07 (br m, 3H), 4.50 (m, 1H), 4.42 (m, 1H), 4.30 (m, 1H), 4.18 (t, J=6.92, 1H), 3.70 (s, 3H), 3.18-2.95 (m, 4H), 1.85-1.35 (m, 4H), 1.30 (s, 10H), 1.20 (br s, 2H); 13C NMR (125 MHz, CDCl3) δ 163.0, 154.6, 143.9-143.8 (3), 141.46, 136.6, 130.0, 128.7, 128.2, 127.9, 127.3, 125.2, 124.5, 120.2 (2), 67.13, 66.8, 53.6, 52.6, 47.3, 41.0, 37.8, 32.6, 29.4, 29.0 (3), 22.17; HRMS (FAB) m/z calcd for C43H49N3O8 (M+H)+ 736.3598, found 736.3623.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09238697B2
Quelldatensatzuspto-grants-2016_01
ORD IDord-6e229c8eb51c4ef5b0607fce9e3dc950
Quellennotizuspto-grants-2016_01