1,2-Dichloroethane → N-Boc-Tyr(Bn)-Lys(Boc)-Trp-NH(CH2)4NHBoc

HRID 2074362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2074362
[NH2:1][C@H:2]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH:28]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[C@H:29]([C:45]([NH:47][C@H:48]([C:61](O)=[O:62])[CH2:49][CH2:50][CH2:51][CH2:52][NH:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])=[O:46])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:33][CH:32]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C=O)C>[NH:28]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[C@H:29]([C:45]([NH:47][C@H:48]([C:61]([NH:1][C@H:2]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)=[O:62])[CH2:49][CH2:50][CH2:51][CH2:52][NH:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])=[O:46])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:33][CH:32]=1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 16735218Trp-NH(CH2)4NHBocHCID 57611779N-Boc-Tyr(Bn)-Lys(Boc)-OH

Produkt 1

HCID 16736779N-Boc-Tyr(Bn)-Lys(Boc)-Trp-NH(CH2)4NHBocAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

compound SP308P. Same procedure as above with Trp-NH(CH2)4NHBoc (152.4 mg, 0.407 mmol), N-Boc-Tyr(Bn)-Lys(Boc)-OH (247.3 mg, 0.407 mmol), EDC (85.8 mg, 0.45 mmol) and HOBt (60.7 mg, 0.45 mmol) in CH2Cl2/DMF (1.8 mL, 1/1). The crude residue was triturated with MeOH/pentane to afford a white solid (255.9 mg, 65%). 1H NMR (300 MHz, DMSO-d6) δ 1.29-1.57 (m, 10H, 3 CH2 Lys, 2 CH2 putrescine), 1.29 (s, 9H, (CH3)3), 1.36 (s, 9H, (CH3)3), 2.64 (m, 1H, CH2 Tyr), 2.86-3.11 (m, 9H, CH2 Lys, CH2 Tyr, CH2 Trp, 2 CH2 putrescine), 4.10 (m, 1H, CHα), 4.26 (m, 1H, CHα), 4.46 (m, 1H, CHα), 5.03 (s, 2H, CH2 (Bn)), 6.70 (broad s, 1H), 6.87-7.4 (m, 15H), 7.56 (d, J=7.6 Hz, 1H), 7.81-7.97 (m, 3H), 10.8 (s, 1H). 13C NMR (75 MHz, DMSO-d6) δ 22.4, 29.2, 32 (3 CH2 Lys), 26.2, 26.7 (2 CH2 putrescine), 27.8 (CH2 Trp), 28, 28.1, 28.2 (3 (CH3)3), 36.3 (CH2 Tyr), 38.2, 39.5, 39.8 (2 CH2 putrescine, CH2 Lys), 52.4, 53.4, 55.8 (CHα Tyr, Lys, Tip), 69 (CH2 (Bn)), 77.2, 78 (2 C(CH3)3), 109.8, 111.1, 114.2, 118.1, 118.4, 120.7, 123.4, 127.3, 127.5, 127.6, 128.3, 130.1, 135.9, 137.1 (19 aromatic C), 154.7, 155.5, 156.7 (Car-O, 2 CO carbamate), 170.7, 171.1, 171.5 (3 CO amide). Anal. Calcd. for C52H73N7O10: C, 65.32; H, 7.70; N, 10.25. Found: C, 65.30; H, 7.64; N, 10.04.

Aufarbeitung

  1. customThe crude residue was triturated with MeOH/pentane

Quellen und Nachweise

ORD-Eintrag
ord-581771c57df94a24b5b9842f94942a4f
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919468B2

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