HRID1775890

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CCCCCCCOc1ccc(-c2cnc(-c3ccc(C[C@H](NC(=O)OCc4ccccc4)C(=O)N4CC(C(=O)OC)C4)cc3)nc2)cc1

HCID117741085

未命名化合物

PRODUCTS

生成物

结构：CCCCCCCOc1ccc(-c2cnc(-c3ccc(C[C@H](N)C(=O)N4CC(C(=O)OC)C4)cc3)nc2)cc1

HCID117740331

未命名化合物

收率 63%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID23938

Palladium

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

Prepared using General Procedure 18: A solution of (S)-methyl 1-(2-(((benzyloxy)carbonyl)amino)-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)-propanoyl)azetidine-3-carboxylate (1.2 g, 1.81 mmol) in MeOH (150 mL) was passed over a 10% Pd/C CatCart (55×4 mm) at 65° C. in a Thales Nanotechnology H-Cube reactor at 2.1 mL/min. The solvent was evaporated and the residue purified by column chromatography (Ammonia/MeOH/DCM) to afford 604 mg (63%) of (S)-methyl 1-(2-amino-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)propanoyl)azetidine-3-carboxylate. LCMS-ESI (m/z) calculated for C31H38N4O4: 530.3. found 531.0 [M+H]+, tR=1.60 min (Method 6).

WORKUP

后处理

customPrepared
customThe solvent was evaporated
customthe residue purified by column chromatography (Ammonia/MeOH/DCM)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f5d0d0655c9742c094cdbc034556ae77
来源数据集: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09260427B2
来源说明: uspto-grants-2016_02

反应 SMILES

C(OC([NH:11][C@@H:12]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[CH:38][CH:37]=3)=[CH:32][N:31]=2)=[CH:26][CH:25]=1)[C:13]([N:15]1[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16]1)=[O:14])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C@@H:12]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:35]=[CH:34][C:33]([C:36]3[CH:37]=[CH:38][C:39]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[CH:40][CH:41]=3)=[CH:32][N:31]=2)=[CH:26][CH:25]=1)[C:13]([N:15]1[CH2:16][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:18]1)=[O:14]