HRID708779

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID74375

Benzoyl chloride, 3-methyl-

C8H7ClO

结构：COC(=O)[C@H](Cc1ccc(-c2ccnc(C)c2C)cc1)NC(=O)[C@@H]1Cc2cc3c(cc2CN1)O[C@@H](c1ccc(OCC2CCCCC2)cc1)CO3.Cl.Cl

HCID66719507

未命名化合物

PRODUCTS

生成物

结构：Cc1cccc(C(=O)N2Cc3cc4c(cc3C[C@H]2C(=O)N[C@@H](Cc2ccc(-c3ccnc(C)c3C)cc2)C(=O)O)OC[C@H](c2ccc(OCC3CCCCC3)cc2)O4)c1

HCID58327433

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

溶剂HCID516892

Sodium Bicarbonate

CHNaO3

PROCEDURE

实验过程

(S)-2-{[(3S,8S)-3-(4-cyclohexylmethoxy-phenyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid methyl ester bis hydrochloride (20 mg) was dissolved in 1:1 EtOAc and saturated aqueous NaHCO3 and 3-methylbenzoyl chloride (3 eq) added. After stirring at room temperature 1 hour, the layers were separated and the organic layer was dried over Na2SO4 and evaporated. The residue was purified by over silica (hexanes to 8:2 hexanes-EtOAc to 6:4 hexanes-EtOAc to 6:4 hexanes-EtOAc+2% MeOH to DCM+3% MeOH). The resulting compound was hydrolyzed according to General Procedure B to give the title compound (15 mg). LCMS (m/z): 795.

WORKUP

后处理

additionadded
customthe layers were separated
dry with materialthe organic layer was dried over Na2SO4
customevaporated
customThe residue was purified by over silica (hexanes to 8:2 hexanes-EtOAc to 6:4 hexanes-EtOAc to 6:4 hexanes-EtOAc+2% MeOH to DCM+3% MeOH)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4676cc742f6c4bfb96d563e0d40caa97
来源数据集: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09175003B2
来源说明: uspto-grants-2015_11

反应 SMILES

Cl.Cl.C[O:4][C:5](=[O:53])[C@@H:6]([NH:22][C:23]([C@@H:25]1[CH2:34][C:33]2[CH:32]=[C:31]3[O:35][CH2:36][C@H:37]([C:39]4[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH:47]5[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]5)=[CH:41][CH:40]=4)[O:38][C:30]3=[CH:29][C:28]=2[CH2:27][NH:26]1)=[O:24])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[C:15]=2[CH3:21])=[CH:10][CH:9]=1.[CH3:54][C:55]1[CH:56]=[C:57]([CH:61]=[CH:62][CH:63]=1)[C:58](Cl)=[O:59]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH:47]1([CH2:46][O:45][C:42]2[CH:41]=[CH:40][C:39]([C@H:37]3[CH2:36][O:35][C:31]4=[CH:32][C:33]5[CH2:34][C@@H:25]([C:23]([NH:22][C@@H:6]([CH2:7][C:8]6[CH:9]=[CH:10][C:11]([C:14]7[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[C:15]=7[CH3:21])=[CH:12][CH:13]=6)[C:5]([OH:53])=[O:4])=[O:24])[N:26]([C:58](=[O:59])[C:57]6[CH:61]=[CH:62][CH:63]=[C:55]([CH3:54])[CH:56]=6)[CH2:27][C:28]=5[CH:29]=[C:30]4[O:38]3)=[CH:44][CH:43]=2)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1