HRID71658

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6228

N,N-Dimethylformamide

C3H7NO

HCID81531

Diisopropylethylamine

C8H19N

HCID638739

(2R,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

C10H13NO3

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：CCCc1cc(C(=O)O)nn1Cc1ccc(-c2ccccc2S(=O)(=O)NC(C)=O)cc1

HCID66757639

未命名化合物

PRODUCTS

生成物

结构：CCCc1cc(C(=O)N[C@H](Cc2ccccc2)[C@@H](O)C(=O)O)nn1Cc1ccc(-c2ccccc2S(=O)(=O)NC(C)=O)cc1

HCID66757852

未命名化合物

收率 97%

CONDITIONS

反应条件

温度: 45 °C

PROCEDURE

实验过程

A solution of 1-(2′-acetylsulfamoylbiphenyl-4-ylmethyl)-5-propyl-1H-pyrazole-3-carboxylic acid (250 mg, 570 μmol), HATU (215 mg, 566 μmol) and DIPEA (592 μL, 3.4 mmol) in DMF (18 mL, 230 mmol) was stirred to pre-activate the acid. After 15 minutes, (2R,3R)-3-amino-2-hydroxy-4-phenylbutyric acid (110 mg, 566 μmol) was added. The resulting solution was stirred at 45° C. overnight. The mixture was concentrated, re-dissolved in water/MeCN/TFA and purified using reverse phase liquid chromatography to yield the title compound (197 mg, 97% purity). MS m/z: [M+H]+ calcd for C32H34N4O7S, 619.22. found 619.6.

WORKUP

后处理

concentrationThe mixture was concentrated
dissolutionre-dissolved in water/MeCN/TFA
custompurified

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-37dbbb980e384507b150930d32e3f1f8
来源数据集: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08822522B2
来源说明: uspto-grants-2014_09

反应 SMILES

[C:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]([CH2:26][CH2:27][CH3:28])=[CH:24][C:23](C(O)=O)=[N:22]2)=[CH:16][CH:15]=1)(=[O:7])=[O:6])(=[O:3])[CH3:2].CN([C:35]([O:39]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C=O)C.[NH2:70][C@H:71]([CH2:77][C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)[C@@H:72]([OH:76])[C:73]([OH:75])=[O:74]>>[C:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]([CH2:26][CH2:27][CH3:28])=[CH:24][C:23]([C:35]([NH:70][C@H:71]([CH2:77][C:78]3[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=3)[C@@H:72]([OH:76])[C:73]([OH:75])=[O:74])=[O:39])=[N:22]2)=[CH:16][CH:15]=1)(=[O:6])=[O:7])(=[O:3])[CH3:2]