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

HRID 592508

反応式

HRID 592508 の反応式
C(N(C(C)C)CC)(C)C.[NH2:10][C@H:11]([C:27]([O:29][CH3:30])=[O:28])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].[NH:31]([C:48]([O:50][CH2:51][CH:52]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[C:58]2[C:53]1=[CH:54][CH:55]=[CH:56][CH:57]=2)=[O:49])[C@H:32]([C:45](O)=[O:46])[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:36][CH:35]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[NH:31]([C:48]([O:50][CH2:51][CH:52]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[C:58]2[C:53]1=[CH:54][CH:55]=[CH:56][CH:57]=2)=[O:49])[C@H:32]([C:45]([NH:10][C@H:11]([C:27]([O:29][CH3:30])=[O:28])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:46])[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[CH:36][CH:35]=1

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6994982methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoateHCID 10895791Fmoc-L-Tyr(tBu)-OH

生成物 1

HCID 131734556Fmoc-Tyr(tBu)-Lys(Z)-OMe収率 97.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  1. washwas washed with 1N HCl (2×20 mL)
  2. concentrationThe organic layer was concentrated in vacuo

出典と根拠

ORDレコード
ord-6e229c8eb51c4ef5b0607fce9e3dc950
出典データセット
uspto-grants-2016_01
特許番号
US09238697B2

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