HRID2293348

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID69179

Bromomethyl 2-naphthyl ketone

C12H9BrO

结构：CC[C@H](C)[C@H](N)C(=O)NCc1ccccc1.O=C(O)[C@@H]1CCCN1

HCID86751513

未命名化合物

PRODUCTS

生成物

结构：CC[C@H](C)[C@H](N)C(=O)N(Cc1ccccc1)C(=O)[C@@H]1CCCN1CC(=O)c1ccc2ccccc2c1

HCID67620037

未命名化合物

收率 80.6%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

Using the procedure described in example 5, treatment of L-proline-L-isoleucine benzylamide (296 mg, 0.93 mmol), with cesium carbonate (0.61 g, 1.87 mmol), and 2-bromo-2'-acetonaphthone (697 mg, 2.80 mmol, 3.0 eq) in acetonitrile (12 mL), provided 364 mg (80%) of L-isoleucine, N-[1-(2-naphth-2-yl-2-oxoethyl)-L-prolyl] benzylamide as a pale yellow oil.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cd6ea2ec42294b9b949e551173051bf5
来源数据集: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05686424
来源说明: uspto-grants-1997_11

反应 SMILES

[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH2:9]([NH:16][C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33]([C:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=1)=[O:34]>C(#N)C>[CH:36]1[C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:43]=[CH:44][C:35]=1[C:33](=[O:34])[CH2:32][N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([N:16]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])=[O:5]