HRID732592

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CCCCC/C=C1/C[C@H]([C@H]2OC(C)(C)N(C(C)=O)[C@H]2Cc2cc(F)cc(F)c2)N(C(=O)OC(C)(C)C)C1

HCID68818416

未命名化合物

HCID178418361

未命名化合物

PRODUCTS

生成物

HCID68815992

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID23938

Palladium

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

Combine (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hex-(Z)-ylidene-pyrrolidine-1-carboxylic acid tert-butyl ester (0.04 g, 0.076 mmol), 10% palladium on carbon (4 mg) and methanol (2 mL) and stir for 2 days under 1 atmosphere of hydrogen. Add filter agent, filter and concentrate under reduced pressure to provide the desired compound as a mixture of isomers (2:1 4(S):4(R); 0.036 g, 90%). Subject isomer mixture to HPLC chromatography under acidic conditions: TFA 0.05% at pH 2.5; Organic solvent: acetonitrile; Gradient from 90 to 95% acetonitrile.

WORKUP

后处理

additionAdd
filtrationfilter agent
filtrationfilter
concentrationconcentrate under reduced pressure

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-596b0beeb0204f4589feaf5fe1eee294
来源数据集: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07585885B2
来源说明: uspto-grants-2009_09

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:12]/[C:11](=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])/[CH2:10][C@@H:9]1[C@H:19]1[O:23][C:22]([CH3:25])([CH3:24])[N:21]([C:26](=[O:28])[CH3:27])[C@H:20]1[CH2:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[C:32]([F:37])[CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][C@@H:9]1[C@H:19]1[O:23][C:22]([CH3:25])([CH3:24])[N:21]([C:26](=[O:28])[CH3:27])[C@H:20]1[CH2:29][C:30]1[CH:31]=[C:32]([F:37])[CH:33]=[C:34]([F:36])[CH:35]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]