HRID650780

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14798

Sodium Hydroxide

HNaO

结构：CCCOc1ccc2c(c1)C(c1ccc(OC)cc1Oc1cnccc1C(=O)O)C(C(=O)[O-])C2c1ccc2c(c1)OCO2

HCID18427634

未命名化合物

PRODUCTS

生成物

结构：CCCOc1ccc2c(c1)C(c1ccc(OC)cc1Oc1cnccc1C(=O)O)C(C(=O)[O-])C2c1ccc2c(c1)OCO2.CCCOc1ccc2c(c1)C(c1ccc(OC)cc1Oc1cnccc1C(=O)O)C(C(=O)[O-])C2c1ccc2c(c1)OCO2.[Na+].[Na+]

HCID86752077

未命名化合物

收率 74%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID3776

Isopropanol

C3H8O

PROCEDURE

实验过程

To a solution of Methyl (1RS, 2SR, 3RS)-3-[2-[(4-Carboxypyridin-3-yl)oxy]-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (90, 0.15 mmol) in isopropanol (2 mL) was added 1M aqueous NaOH (0.3 mL, 0.3 mmol). The resulting mixture was heated to reflux for 12 h, then concentrated under reduced pressure. The residue was partitioned between dilute HCl and ethyl acetate. The ethyl acetate extract was washed with water and dried (Mg2SO4). The solvent was removed in vacuo. The residue was purified by flash column chromatography (silica gel, 30% ethyl acetate/hexanes containing 5% of acetic acid) to afford the title compound (65 mg, 74%); m.p. 220-222° C. (dec.) (disodium salt).

WORKUP

后处理

temperatureThe resulting mixture was heated
temperatureto reflux for 12 h
concentrationconcentrated under reduced pressure
customThe residue was partitioned between dilute HCl and ethyl acetate
extractionThe ethyl acetate extract
washwas washed with water
dry with materialdried (Mg2SO4)
customThe solvent was removed in vacuo
customThe residue was purified by flash column chromatography (silica gel, 30% ethyl acetate/hexanes containing 5% of acetic acid)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1f30411e22e647f19989584387230883
来源数据集: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06274737B1
来源说明: uspto-grants-2001_08

反应 SMILES

[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[CH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH2:29][CH2:30][CH3:31])[CH:26]=2)[CH:21]([C:32]2[CH:37]=[CH:36][C:35]3[O:38][CH2:39][O:40][C:34]=3[CH:33]=2)[CH:20]1[C:41]([O-:43])=[O:42])([OH:3])=[O:2].[OH-].[Na+:45]>C(O)(C)C>[Na+:45].[Na+:45].[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[CH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH2:29][CH2:30][CH3:31])[CH:26]=2)[CH:21]([C:32]2[CH:37]=[CH:36][C:35]3[O:38][CH2:39][O:40][C:34]=3[CH:33]=2)[CH:20]1[C:41]([O-:43])=[O:42])([OH:3])=[O:2].[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[CH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH2:29][CH2:30][CH3:31])[CH:26]=2)[CH:21]([C:32]2[CH:37]=[CH:36][C:35]3[O:38][CH2:39][O:40][C:34]=3[CH:33]=2)[CH:20]1[C:41]([O-:43])=[O:42])([OH:3])=[O:2]