HRID537627

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2723939

1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

C8H18ClN3

2 次

结构：CC(C)(C)OC(=O)NCCCC[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O

HCID13585941

N~6~-(tert-Butoxycarbonyl)-N~2~-{[(9H-fluoren-9-yl)methoxy]carbonyl}-D-lysine

C26H32N2O6

2 次

结构：CC(C)C[C@H](NC(=O)[C@H](N)CCCCNC(=O)OC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)OCc1ccccc1

HCID131731957

未命名化合物

PRODUCTS

生成物

结构：CC(C)C[C@H](NC(=O)[C@@H](CCCCNC(=O)OC(C)(C)C)NC(=O)[C@@H](CCCCNC(=O)OC(C)(C)C)NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)N[C@@H](CC(C)C)C(=O)OCc1ccccc1

HCID131731956

未命名化合物

收率 85%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID75771

1-Hydroxybenzotriazole

C6H5N3O

溶剂HCID6212

Chloroform

CHCl3

2 次

PROCEDURE

实验过程

The obtained wet crystals of D-Lys(Boc)-Leu-Leu-OBzl (2-MeO-4-OC12OC22) were dissolved in chloroform (15 mL), Fmoc-D-Lys(Boc)-OH (444 mg, 948 μmol) and HOBt (12.8 mg, 94.7 μmol) were added at room temperature, and EDC HCl (200 mg, 1.04 mmol) was further added under ice-cooling. The mixture was warmed to room temperature and stirred overnight. Chloroform (20 mL), Fmoc-D-Lys(Boc)-OH (89 mg, 190 μmol) and EDC.HCl (40 mg, 210 μmol) were added, and the mixture was further stirred for 1 hr and concentrated under reduced pressure. The residue was precipitated with methanol (15 mL) to give Fmoc-D-Lys(Boc)-D-Lys(Boc)-Leu-Leu-OBzl (2-MeO-4-OC12OC22) (1.35 g, 85% yield relative to Bzl (2-MeO-4-OC12OC22)OH).

WORKUP

后处理

temperaturecooling
stirringthe mixture was further stirred for 1 hr
concentrationconcentrated under reduced pressure
customThe residue was precipitated with methanol (15 mL)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1769a37cff0046a0bf2daf328e8f6032
来源数据集: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08859732B2
来源说明: uspto-grants-2014_10

反应 SMILES

[NH2:1][C@@H:2]([C:15]([NH:17][C@H:18]([C:23]([NH:25][C@H:26]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[NH:41]([C:58]([O:60][CH2:61][CH:62]1[C:74]2[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=2)[C:68]2[C:63]1=[CH:64][CH:65]=[CH:66][CH:67]=2)=[O:59])[C@@H:42]([C:55](O)=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49].CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl.C1C=CC2N(O)N=NC=2C=1>[NH:41]([C:58]([O:60][CH2:61][CH:62]1[C:74]2[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=2)[C:68]2[C:63]1=[CH:64][CH:65]=[CH:66][CH:67]=2)=[O:59])[C@@H:42]([C:55]([NH:1][C@@H:2]([C:15]([NH:17][C@H:18]([C:23]([NH:25][C@H:26]([C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:24])[CH2:19][CH:20]([CH3:21])[CH3:22])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:49]