HRID391764

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID81531

Diisopropylethylamine

C8H19N

结构：CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F

HCID2733084

Methanaminium, N-[(1H-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methyl-, hexafluorophosphate(1-) (1:1)

C11H16F6N5OP

结构：COC(=O)[C@@H](N)Cc1ccc(-c2ccc(C#N)cc2)cc1

HCID59337513

未命名化合物

结构：CC(C)(C)OC(=O)N1Cc2cc3c(cc2CC1C(=O)O)OC[C@H](c1ccc(OCc2ccc(Cl)c(Cl)c2)cc1)O3

HCID66719307

未命名化合物

PRODUCTS

生成物

结构：COC(=O)[C@H](Cc1ccc(-c2ccc(C#N)cc2)cc1)NC(=O)C1Cc2cc3c(cc2CN1C(=O)OC(C)(C)C)O[C@@H](c1ccc(OCc2ccc(Cl)c(Cl)c2)cc1)CO3

HCID67249301

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

(S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-2,3,8,9-tetrahydro-6H-[1,4]dioxino[2,3-g]isoquinoline-7,8-dicarboxylic acid 7-tert-butyl ester, HBTU and DIEA were dissolved in DMF (20 mL). (S)-2-Amino-3-(4′-cyano-biphenyl-4-yl)-propionic acid methyl ester was added and the mixture stirred at r.t. for 16 h. The reaction mixture was poured into 1 N HCl and extracted with ethyl acetate. The organic extracts were combined and washed with 1 N HCl and 10% sodium carbonate, concentrated and purified by column chromatography on silica gel (hexanes-ethyl acetate) to afford the product (4.9 g). LCMS (m/z) 851.

WORKUP

后处理

extractionextracted with ethyl acetate
washwashed with 1 N HCl and 10% sodium carbonate
concentrationconcentrated
custompurified by column chromatography on silica gel (hexanes-ethyl acetate)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d7b64f95ed834f28ab4c21fd054c2550
来源数据集: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08383644B2
来源说明: uspto-grants-2013_02

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH:17]([C:18]([OH:20])=O)[CH2:16][C:15]2[CH:14]=[C:13]3[O:21][CH2:22][C@H:23]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]5[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=5)=[CH:27][CH:26]=4)[O:24][C:12]3=[CH:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:74][O:75][C:76](=[O:94])[C@@H:77]([NH2:93])[CH2:78][C:79]1[CH:84]=[CH:83][C:82]([C:85]2[CH:90]=[CH:89][C:88]([C:91]#[N:92])=[CH:87][CH:86]=2)=[CH:81][CH:80]=1.Cl>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:17]([C:18](=[O:20])[NH:93][C@H:77]([C:76]([O:75][CH3:74])=[O:94])[CH2:78][C:79]2[CH:80]=[CH:81][C:82]([C:85]3[CH:90]=[CH:89][C:88]([C:91]#[N:92])=[CH:87][CH:86]=3)=[CH:83][CH:84]=2)[CH2:16][C:15]2[CH:14]=[C:13]3[O:21][CH2:22][C@H:23]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]5[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=5)=[CH:27][CH:26]=4)[O:24][C:12]3=[CH:11][C:10]=2[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]