HRID1375708

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID25517

未命名化合物

HCID78288

Glycine, N-[(1,1-dimethylethoxy)carbonyl]-

C7H13NO4

HCID2723939

1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

C8H18ClN3

$结构：CC(C)(C)[Si](C)(C)OC/C(=C(\CO)c1ccc(S(C)(=O)=O)cc1)c1ccccc1$

HCID58787782

未命名化合物

PRODUCTS

生成物

$结构：CC(C)(C)OC(=O)NCC(=O)OC/C(=C(\CO[Si](C)(C)C(C)(C)C)c1ccccc1)c1ccc(S(C)(=O)=O)cc1$

HCID58787788

未命名化合物

收率 98.4%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a solution of 16.4 g of (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methyl-sulfonyl)phenyl]-3-phenylbut-2-en-1-ol, 1.92 g of DMAP and 7.30 g of Boc-Glycine in 125 mL of CH2Cl2 at 0° C. was added 8.0 g of EDCl. The reaction mixture was stirred for 4 h. Then saturated ammonium chloride solution was added and extracted with EtOAc. The organic layer was combined, washed with brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography over silica gel (5–55% EtOAc/hexane) to afford 22 g of the titled compound as a colorless oil. 1H (500 MHz, acetone-d6): δ 7.67 (d, 2H), 7.34 (d, 2H), 7.13–7.04 (m, 5H), 6.26 (br s, NH), 5.23 (s, 2H), 4.76 (s, 2H), 3.73 (d, 2H), 3.02 (s, 3H), 1.40 (s, 9H), 0.81 (s, 9H), −0.01 (s, 6H).

WORKUP

后处理

extractionextracted with EtOAc
washwashed with brine
dry with materialdried over Na2SO4
customThe solvent was evaporated
customthe residue was purified by flash chromatography over silica gel (5–55% EtOAc/hexane)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8aa874796c8348618df175811314553b
来源数据集: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07169809B2
来源说明: uspto-grants-2007_01

反应 SMILES

[Si:1]([O:8][CH2:9]/[C:10](/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[C:11](/[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)\[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:30]([NH:37][CH2:38][C:39](O)=[O:40])([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].CCN=C=NCCCN(C)C.Cl.[Cl-].[NH4+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:33]([O:32][C:30]([NH:37][CH2:38][C:39]([O:13][CH2:12]/[C:11](/[C:14]1[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=1)=[C:10](/[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)\[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[O:40])=[O:31])([CH3:36])([CH3:35])[CH3:34]