HRID490951

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID3939

Lithium hydroxide anhydrous

HLiO

结构：COC(=O)C(OP(=O)(O)[C@@H](NS(=O)(=O)Cc1ccccc1)C(C)C)c1cccc(NC(=NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)c1

HCID178501872

未命名化合物

PRODUCTS

生成物

结构：CC(C)[C@H](NS(=O)(=O)Cc1ccccc1)P(=O)(O)OC(C(=O)O)c1cccc(NC(=NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)c1

HCID178448389

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

溶剂HCID962

Water

H2O

PROCEDURE

实验过程

To a slurry of 2-(3-(N′,N″-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1R)-(1-(benzylsulfonyl)amino-2-methylpropyl)(hydroxy)phosphinoyloxy)ethanoic acid methyl ester (0.53 mmol) in 6 mL of methanol and 3 mL of H2O was added LiOH (124.3 mg, 5.3 mmol). After stirring for 6 hours, the solution was acidified to pH 2 with concentrated HCl and extracted with methylene chloride (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give 2-(3-(N′,N″-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1R)-(1-(benzylsulfonyl)amino-2-methylpropyl)(hydroxy)phosphinoyloxy)ethanoic acid as a yellow oil that was used without further purification in the following step.

WORKUP

后处理

extractionextracted with methylene chloride (3×)
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-620d760297e14bb3a7a82379fce078b0
来源数据集: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07528173B2
来源说明: uspto-grants-2009_05

反应 SMILES

C[O:2][C:3](=[O:48])[CH:4]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[N:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH:25]=1)[O:5][P:6]([C@@H:9]([NH:13][S:14]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH:10]([CH3:12])[CH3:11])([OH:8])=[O:7].[Li+].[OH-].Cl>CO.O>[C:36]([O:35][C:33]([N:32]=[C:31]([NH:40][C:41]([O:43][C:44]([CH3:46])([CH3:45])[CH3:47])=[O:42])[NH:30][C:26]1[CH:25]=[C:24]([CH:4]([O:5][P:6]([C@@H:9]([NH:13][S:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:15])=[O:16])[CH:10]([CH3:12])[CH3:11])([OH:8])=[O:7])[C:3]([OH:48])=[O:2])[CH:29]=[CH:28][CH:27]=1)=[O:34])([CH3:37])([CH3:38])[CH3:39]