HRID966464

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID311

Citric Acid

C6H8O7

HCID887

Methanol

CH4O

HCID3939

Lithium hydroxide anhydrous

HLiO

$反应SMILES：C=C/C=C(\C)C(NCCCCCC(=O)n1ccc2c3c(ccc21)NC(C(=O)n1ccc2c4c(ccc21)NC(C(=O)n1ccc2c5c(ccc21)NC(C(=O)OC)C5)C4)C3)(c1ccccc1)c1ccc(OC)cc1$

HCID86588459

未命名化合物

PRODUCTS

产物

$反应SMILES：C=C/C=C(\C)C(NCCCCCC(=O)n1ccc2c3c(ccc21)NC(C(=O)n1ccc2c4c(ccc21)NC(C(=O)n1ccc2c5c(ccc21)NC(C(=O)O)C5)C4)C3)(c1ccccc1)c1ccc(OC)cc1$

HCID86588460

未命名化合物

收率 60.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

CONDITIONS

反应条件

温度: 55 °C

PROCEDURE

实验过程

A suspension of 10 (270 mg, 0.28 mmol) in a mixture of THF (6 ml), MeOH (4 ml) and 4M LiOH (2 ml) was stirred at 55° C. for 30 h. The reaction was cooled and neutralized to pH 6 with cold 10% citric acid. Insoluble material was collected by filtration and washed with water, MeOH and ether. Drying under vacuum afforded 160 mg (60%) of the title compound 11. By HPLC analysis this product contained ˜5% of unreacted 10. The crude acid was used in the next step without additional purification.

WORKUP

后处理

temperatureThe reaction was cooled
filtrationInsoluble material was collected by filtration
washwashed with water, MeOH and ether
customDrying under vacuum

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-8ff68324979542a49f02662020de2471
来源数据集: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US06951930B2
来源说明: uspto-grants-2005_10

反应SMILES

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]2[C:40]3[C:32](=[C:33]4[C:37](=[CH:38][CH:39]=3)[NH:36][CH:35]([C:41]([N:43]3[C:54]5[C:46](=[C:47]6[C:51](=[CH:52][CH:53]=5)[NH:50][CH:49]([C:55]([N:57]5[C:68]7[C:60](=[C:61]8[C:65](=[CH:66][CH:67]=7)[NH:64][CH:63]([C:69]([O:71]C)=[O:70])[CH2:62]8)[CH:59]=[CH:58]5)=[O:56])[CH2:48]6)[CH:45]=[CH:44]3)=[O:42])[CH2:34]4)[CH:31]=[CH:30]2)=[O:28])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)/[C:10](/[CH3:14])=[CH:11]/[CH:12]=[CH2:13])=[CH:5][CH:4]=1.CO.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]2[C:40]3[C:32](=[C:33]4[C:37](=[CH:38][CH:39]=3)[NH:36][CH:35]([C:41]([N:43]3[C:54]5[C:46](=[C:47]6[C:51](=[CH:52][CH:53]=5)[NH:50][CH:49]([C:55]([N:57]5[C:68]7[C:60](=[C:61]8[C:65](=[CH:66][CH:67]=7)[NH:64][CH:63]([C:69]([OH:71])=[O:70])[CH2:62]8)[CH:59]=[CH:58]5)=[O:56])[CH2:48]6)[CH:45]=[CH:44]3)=[O:42])[CH2:34]4)[CH:31]=[CH:30]2)=[O:28])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)/[C:10](/[CH3:14])=[CH:11]/[CH:12]=[CH2:13])=[CH:5][CH:4]=1