HRID2242421

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81531

Diisopropylethylamine

C8H19N

结构：CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F

HCID9886157

Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

C10H15F6N6OP

结构：CCC[C@H](NC(=O)C1CC(Oc2cc(-c3ccccc3)nc3cc(OC)ccc23)C=C1C(=O)O)C(=O)OC(C)(C)C

HCID59204172

未命名化合物

HCID68490522

未命名化合物

PRODUCTS

生成物

结构：CCC[C@H](NC(=O)[C@H]1C[C@H](Oc2cc(-c3ccccc3)nc3cc(OC)ccc23)C=C1C(=O)N[C@H](C(=O)N[C@H](C(=O)OC)C1CCCCC1)C(C)C)C(=O)OC(C)(C)C

HCID11468492

未命名化合物

收率 7.5%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

溶剂HCID1140

Toluene

C7H8

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

The acid 11 (0.051 g, 0.087 mmol) and (2-amino-3-methyl-butyrylamino)-cyclohexyl-acetic acid methyl ester (0.054 g, 0.21 mmol) were dissolved in DMF (1.5 mL) and cooled in an ice-bath. DIPEA (16 mg, 0.12 mmol) and HATU (47 mg, 0.13 mmol) were added. After two and a half hours the mixture was co-concentrated with toluene and methanol and then purified by flash column chromatography (toluene/ethyl acetate 3:1). Further purification was performed on HPLC (90% MeOH+0.2% TEA). This gave after co-concentration the two diastereomers 19a (9.4 mg, 13%) and 19b (5.3 mg, 7%) as slightly yellow syrups. After lyophilisation 19a and 19b were collected as white powders:

WORKUP

后处理

temperaturecooled in an ice-bath
custompurified by flash column chromatography (toluene/ethyl acetate 3:1)
customFurther purification

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ccb28e3207854bdd855bd8f711b60cd2
来源数据集: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07671032B2
来源说明: uspto-grants-2010_03

反应 SMILES

[C:1]([O:5][C:6]([C@@H:8]([NH:12][C:13]([CH:15]1[C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]([O:23][C:24]2[C:33]3[C:28](=[CH:29][C:30]([O:34][CH3:35])=[CH:31][CH:32]=3)[N:27]=[C:26]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:25]=2)[CH2:16]1)=[O:14])[CH2:9][CH2:10][CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:42][O:43][C:44](=[O:60])[CH:45]([NH:52][C:53](=[O:59])[CH:54]([NH2:58])[CH:55]([CH3:57])[CH3:56])[CH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CO.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[C@@H:8]([NH:12][C:13]([C@H:15]1[CH2:16][C@H:17]([O:23][C:24]2[C:33]3[C:28](=[CH:29][C:30]([O:34][CH3:35])=[CH:31][CH:32]=3)[N:27]=[C:26]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:25]=2)[CH:18]=[C:19]1[C:20](=[O:22])[NH:58][C@H:54]([C:53](=[O:59])[NH:52][C@@H:45]([CH:46]1[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]1)[C:44]([O:43][CH3:42])=[O:60])[CH:55]([CH3:57])[CH3:56])=[O:14])[CH2:9][CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2]