HRID2206345

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：O=C1O[C@H]([C@@H](O)CO)C([O-])=C1O.[Na+]

HCID23667548

Sodium L-ascorbate

C6H7NaO6

结构：C#CC(=O)NCCCCC(NC(=O)C#C)C(=O)NC(CCCCN)C(=O)O

HCID89600888

未命名化合物

结构：[N-]=[N+]=NCCCCC(NC(=O)CCCCCCC(=O)NCCCC[C@H](NC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)C(=O)O

HCID117700439

未命名化合物

PRODUCTS

生成物

结构：NCCCCC(NC(=O)C(CCCCNC(=O)c1cn(CCCCC(NC(=O)CCCCCCC(=O)NCCCC[C@H](NC(=O)NC(CCC(=O)O)C(=O)O)C(=O)O)C(=O)O)nn1)NC(=O)c1nn[nH]c1CCCCC(NC(=O)CCCCCCC(=O)NCCCC[C@H](NC(=O)NC(CCC(=O)O)C(=O)O)C(=O)O)C(=O)O)C(=O)O

HCID178511006

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID8895

Cupric acetate

C4H6CuO4

溶剂HCID71401949

2-Methylpropan-2-ol--water (1/1)

C4H12O2

PROCEDURE

实验过程

Compound 1 (49 mg, 76.7 μM) and 4 (0.5 eq, 14.5 mg, 38.3 μM) were dissolved in 1 mL H2O/t-BuOH (1/1). To that solution, sodium ascorbate (6 mg, 30 μM) and Cu(OAc)2 (3 mg, 15 μM) were added consecutively, the mixture was purged with N2 gas and stirred at ambient temperature overnight. Compound 2 was purified using C18 SepPak® Vac 2 g column through which the product was successfully eluted using 70/30 water/acetonitrile (0.1% TFA). Compound 2 was further purified by HPLC (Method 1). Rt: 13.9 min. ESI-MS m/Z: 1638 [M+H]+.

WORKUP

后处理

customthe mixture was purged with N2 gas
customCompound 2 was purified
washwas successfully eluted
customCompound 2 was further purified by HPLC (Method 1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2777fbe4486642b7ba1004b52714def4
来源数据集: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09371360B2
来源说明: uspto-grants-2016_06

反应 SMILES

[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([C:42]([OH:44])=[O:43])[NH:9][C:10](=[O:41])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:40])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]([C:37]([OH:39])=[O:38])[NH:24][C:25](=[O:36])[NH:26][C@H:27]([C:33]([OH:35])=[O:34])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[N+:2]=[N-:3].[NH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH:50]([NH:54][C:55](=[O:71])[CH:56]([NH:66][C:67](=[O:70])[C:68]#[CH:69])[CH2:57][CH2:58][CH2:59][CH2:60][NH:61][C:62](=[O:65])[C:63]#[CH:64])[C:51]([OH:53])=[O:52].[O:72]=[C:73]1[O:79][C@H:78]([C@H:80]([CH2:82]O)O)[C:76]([O-])=[C:74]1O.[Na+]>O.CC(O)(C)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH:50]([NH:54][C:55](=[O:71])[CH:56]([NH:66][C:67]([C:68]1[N:1]=[N:2][NH:3][C:69]=1[CH2:82][CH2:80][CH2:78][CH2:76][CH:74]([C:73]([OH:79])=[O:72])[NH:9][C:10](=[O:41])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:40])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]([C:37]([OH:39])=[O:38])[NH:24][C:25](=[O:36])[NH:26][CH:27]([C:33]([OH:35])=[O:34])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:70])[CH2:57][CH2:58][CH2:59][CH2:60][NH:61][C:62]([C:63]1[N:3]=[N:2][N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([C:42]([OH:44])=[O:43])[NH:9][C:10](=[O:41])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:40])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]([C:37]([OH:39])=[O:38])[NH:24][C:25](=[O:36])[NH:26][CH:27]([C:33]([OH:35])=[O:34])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:64]=1)=[O:65])[C:51]([OH:53])=[O:52]