HRID539136

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8083

Morpholine

C4H9NO

结构：C=CCOC(=O)C[C@H](O)[C@H](NC(=O)[C@@H](C)NC(=O)[C@H](NC(=O)C[C@H](O)/C=C/CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C)C(C)C

HCID59223145

未命名化合物

PRODUCTS

生成物

结构：CC(C)[C@@H](NC(=O)[C@@H](C)NC(=O)[C@H](NC(=O)C[C@H](O)/C=C/CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C)[C@@H](O)CC(=O)O

HCID59223153

未命名化合物

收率 100%

AUXILIARIES

试剂、催化剂与溶剂

结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

To a solution of 7 (152.2 mg, 0.2 mmol), Pd(PPh3)4 (23.2 mg, 0.02 mmol) in dry methanol (6 mL) under argon was added morpholine (35 μL, 0.40 mmol) which was allowed to stir for 2 h. The reaction mixture was concentrated in vacuo, purification by column chromatography on silica (eluent 0:1-5:95-10:90-10:90+0.5% AcOH MeOH/CH2Cl2) to give a yellow solid 8 (137 mg, 0.18 mmol, 100%): Rf 0.19 MeOH/CH2Cl2 (1:9+0.5% AcOH); IR (thin film) 3271 (b), 2962 (m), 2926 (m), 1624 (s), 1536 (m) cm−1.

WORKUP

后处理

concentrationThe reaction mixture was concentrated in vacuo, purification by column chromatography on silica (eluent 0:1-5:95-10:90-10:90+0.5% AcOH MeOH/CH2Cl2)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e17863cda9fa4514bd3051780909d987
来源数据集: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08865655B2
来源说明: uspto-grants-2014_10

反应 SMILES

C([O:4][C:5](=[O:55])[CH2:6][C@H:7]([OH:54])[C@H:8]([NH:12][C:13](=[O:53])[C@H:14]([NH:16][C:17](=[O:52])[C@H:18]([NH:22][C:23](=[O:51])[CH2:24][C@H:25]([OH:50])/[CH:26]=[CH:27]/[CH2:28][CH2:29][S:30][C:31]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:19]([CH3:21])[CH3:20])[CH3:15])[CH:9]([CH3:11])[CH3:10])C=C.N1CCOCC1>CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:54][C@H:7]([C@H:8]([NH:12][C:13](=[O:53])[C@H:14]([NH:16][C:17](=[O:52])[C@H:18]([NH:22][C:23](=[O:51])[CH2:24][C@H:25]([OH:50])/[CH:26]=[CH:27]/[CH2:28][CH2:29][S:30][C:31]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH:19]([CH3:20])[CH3:21])[CH3:15])[CH:9]([CH3:11])[CH3:10])[CH2:6][C:5]([OH:55])=[O:4]