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

HRID 2074362노트

반응식

HRID 2074362 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 16736779N-Boc-Tyr(Bn)-Lys(Boc)-Trp-NH(CH2)4NHBoc수율 65.8%

시약·촉매·용매 1

HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

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.

후처리

  1. customThe crude residue was triturated with MeOH/pentane

출처 및 근거

ORD 기록
ord-581771c57df94a24b5b9842f94942a4f
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919468B2

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