HRID1433263

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2723923

Formic acid, ammonium salt

CH5NO2

2 次

结构：CC(C)N(CC[C@H](c1ccccc1)c1cc(CCCCOCCCCCCNC[C@H](O[Si](C)(C)C(C)(C)C)c2ccc(OCc3ccccc3)c(NS(C)(=O)=O)c2)ccc1O)C(C)C

HCID57933222

未命名化合物

PRODUCTS

生成物

HCID222

Ammonia gas

H3N

结构：CC(C)N(CC[C@H](c1ccccc1)c1cc(CCCCOCCCCCCNC[C@H](O[Si](C)(C)C(C)(C)C)c2ccc(O)c(NS(C)(=O)=O)c2)ccc1O)C(C)C

HCID57933211

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID9942167

Palladium hydroxide

H2O2Pd

3 次

溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

N-{2-(Benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]phenyl}methanesulfonamide (Preparation 27, 530 mg, 0.55 mmol) was dissolved in ethanol and ammonium formate (700 mg, 10.9 mmol) and 10% palladium hydroxide on carbon (100 mg) was added. The reaction was heated under reflux for 12 hours, cooled to room temperature and further ammonium formate (600 mg, 9.37 mmol) and 10% palladium hydroxide on carbon (60 mg) added. The reaction was heated under reflux for 3 hours, cooled to room temperature and further 10% palladium hydroxide on carbon (60 mg) added. The reaction was heated under reflux for 3 hours, cooled to room temperature and filtered through Arbocel™. The filtrate solvent was removed in vacuo and the oil was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (80/20/2.0 by volume) to furnish the title compound as a yellow oil, 420 mg.

WORKUP

后处理

temperatureThe reaction was heated
temperatureunder reflux for 12 hours
temperatureThe reaction was heated
temperatureunder reflux for 3 hours
temperaturecooled to room temperature
temperatureThe reaction was heated
temperatureunder reflux for 3 hours
temperaturecooled to room temperature
filtrationfiltered through Arbocel™
customThe filtrate solvent was removed in vacuo
customthe oil was purified by column chromatography on silica gel eluting with dichloromethane

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-9f1840b28bfa48cf94ebc3a37810c24e
来源数据集: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07612084B2
来源说明: uspto-grants-2009_11

反应 SMILES

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:52][Si:53]([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:55])[CH3:54])[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([C@@H:36]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:37][CH2:38][N:39]([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])[CH:30]=2)=[CH:11][C:10]=1[NH:60][S:61]([CH3:64])(=[O:63])=[O:62])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[NH3:17].[Si:53]([O:52][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:60][S:61]([CH3:64])(=[O:62])=[O:63])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([C@@H:36]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH2:37][CH2:38][N:39]([CH:40]([CH3:42])[CH3:41])[CH:43]([CH3:45])[CH3:44])[CH:30]=1)([C:56]([CH3:59])([CH3:57])[CH3:58])([CH3:55])[CH3:54]