HRID391861

反应详情

EQUATION

反应方程式

REACTANTS

反应物

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：CN1C[C@H](c2ccc(OCc3ccc(Cl)c(Cl)c3)cc2)Oc2cc3c(cc21)CC(C(=O)O)N(C(=O)OC(C)(C)C)C3

HCID66719462

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)CN3C

HCID66719482

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

To a stirring solution of (S)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-1-methyl-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6,7-dicarboxylic acid 6-tert-butyl ester, HBTU (95 mg) and DIEA in DMF (5 mL) was added (S)-2-amino-3-(4′-cyano-biphenyl-4-yl)-propionic acid methyl ester (79 mg). After 4 hours a sufficient amount of water was added and the mixture was extracted with ethyl acetate. The organic was washed with 1 N HCl, saturated NaHCO3 and brine, and dried over sodium sulfate. The solvent was removed under reduced pressure to provide the crude amide. The residue was purified by column chromatography on silica gel (hexanes/ethyl acetate from 80:20 to 60:40) to afford the product (180 mg).

WORKUP

后处理

extractionthe mixture was extracted with ethyl acetate
washThe organic was washed with 1 N HCl, saturated NaHCO3 and brine
dry with materialdried over sodium sulfate
customThe solvent was removed under reduced pressure
customto provide the crude amide
customThe residue was purified by column chromatography on silica gel (hexanes/ethyl acetate from 80:20 to 60:40)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d1189dcb586e48c4b7551ee72aa3c3f7
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:21]([C:22]([OH:24])=O)[CH2:20][C:19]2[CH:18]=[C:17]3[C:12]([O:13][C@@H:14]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]5[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=5)=[CH:28][CH:27]=4)[CH2:15][N:16]3[CH3:25])=[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.[CH3:75][O:76][C:77](=[O:95])[C@@H:78]([NH2:94])[CH2:79][C:80]1[CH:85]=[CH:84][C:83]([C:86]2[CH:91]=[CH:90][C:89]([C:92]#[N:93])=[CH:88][CH:87]=2)=[CH:82][CH:81]=1>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH:21]([C:22](=[O:24])[NH:94][C@H:78]([C:77]([O:76][CH3:75])=[O:95])[CH2:79][C:80]2[CH:81]=[CH:82][C:83]([C:86]3[CH:91]=[CH:90][C:89]([C:92]#[N:93])=[CH:88][CH:87]=3)=[CH:84][CH:85]=2)[CH2:20][C:19]2[CH:18]=[C:17]3[C:12]([O:13][C@@H:14]([C:26]4[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]5[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=5)=[CH:30][CH:31]=4)[CH2:15][N:16]3[CH3:25])=[CH:11][C:10]=2[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]