HRID618145

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14798

Sodium Hydroxide

HNaO

结构：CCOC(=O)C[C@H](N)CCc1c[nH]c2ccccc12.CN(CC(=O)O)C(=O)CCCc1ccnc(C(=O)OC(C)(C)C)c1N

HCID67601154

未命名化合物

PRODUCTS

生成物

HCID86596525

Ethanol ammonium hydroxide water

C2H13NO3

结构：CN(CC(=O)O)C(=O)CCCc1ccnc(N)c1.N[C@H](CCc1c[nH]c2ccccc12)CC(=O)O

HCID86754473

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

Ester 4-5 (20 mg, 34 μmol) was dissolved in 350 μL EtOH, then 1 N NaOH (85 μL, 85 μmol) was added. After 2 h the reaction was diluted with EtOAc, washed with 10% KHSO4 and brine, dried (MgSO4), filtered and concentrated. The residue was dissolved in 1 mL CH2Cl2, treated with 1 mL TFA for 1 h, then concentrated and azeotroped with toluene. Flash chromatography (silica, 50:1:1, EtOH/H2O/NH4OH) provided 4-6 as an off-white solid.

WORKUP

后处理

washwashed with 10% KHSO4 and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
dissolutionThe residue was dissolved in 1 mL CH2Cl2
additiontreated with 1 mL TFA for 1 h
concentrationconcentrated
customazeotroped with toluene

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-15151bcfb982467eb47379859d4c787b
来源数据集: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05952306
来源说明: uspto-grants-1999_09

反应 SMILES

[C:1]([C:8]1[C:13](N)=[C:12]([CH2:15][CH2:16][CH2:17][C:18]([N:20]([CH2:22][C:23]([OH:25])=[O:24])[CH3:21])=[O:19])[CH:11]=[CH:10][N:9]=1)(OC(C)(C)C)=[O:2].C([O:28][C:29](=[O:44])[CH2:30][C@@H:31]([CH2:33][CH2:34][C:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[NH:37][CH:36]=1)[NH2:32])C.[OH-:45].[Na+]>CCO.CCOC(C)=O>[CH3:8][CH2:1][OH:2].[OH2:28].[NH4+:9].[OH-:45].[NH2:32][C:8]1[CH:13]=[C:12]([CH2:15][CH2:16][CH2:17][C:18]([N:20]([CH2:22][C:23]([OH:25])=[O:24])[CH3:21])=[O:19])[CH:11]=[CH:10][N:9]=1.[NH:37]1[C:38]2[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:35]([CH2:34][CH2:33][C@H:31]([CH2:30][C:29]([OH:44])=[O:28])[NH2:32])=[CH:36]1