HRID2223331

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID12522

Succinamic acid

C4H7NO3

HCID75771

1-Hydroxybenzotriazole

C6H5N3O

HCID81531

Diisopropylethylamine

C8H19N

结构：N#Cc1ccc(C[C@@]23C[C@H](N)CN2C(=O)N(c2cc(Cl)cc(Cl)c2)C3=O)cc1

HCID11281440

未命名化合物

PRODUCTS

生成物

结构：N#Cc1ccc(C[C@@]23C[C@H](NC(=O)CCC(N)=O)CN2C(=O)N(c2cc(Cl)cc(Cl)c2)C3=O)cc1

HCID10239341

未命名化合物

收率 70.3%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID11

1,2-Dichloroethane

C2H4Cl2

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

A mixture of (5S,7S)-5-(4-cyanobenzyl)-3-(3,5-dichlorophenyl)-7-amino-1,3-diazabicyclo[3.3.0]octane-2,4-dione (82.7 mg), succinamic acid (45.86 mg), EDC (93.12 mg), HOBT (61.24 mg) and DIEA (104.79 μL) in THF (5 mL) was stirred overnight at room temperature. The reaction mixture was concentrated and purified by high performance liquid chromatography (HPLC) (Beckman 5μ C18 column; eluted with a gradient of H2O/MeCN (10-100%)/0.1% TFA) to give 72 mg of the titled compound. MS (m/z) 536 (MNa+).

WORKUP

后处理

concentrationThe reaction mixture was concentrated
custompurified by high performance liquid chromatography (HPLC) (Beckman 5μ C18 column
washeluted with a gradient of H2O/MeCN (10-100%)/0.1% TFA)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-dbd7c1e47bb64ee990132b77bc035511
来源数据集: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07375128B2
来源说明: uspto-grants-2008_05

反应 SMILES

[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][C@@:8]23[CH2:15][C@H:14]([NH2:16])[CH2:13][N:12]2[C:11](=[O:17])[N:10]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[C:9]3=[O:26])=[CH:5][CH:4]=1)#[N:2].[C:29](O)(=[O:35])[CH2:30][CH2:31][C:32]([NH2:34])=[O:33].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1.C(Cl)CCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C@@:8]23[CH2:15][C@H:14]([NH:16][C:29](=[O:35])[CH2:30][CH2:31][C:32](=[O:33])[NH2:34])[CH2:13][N:12]2[C:11](=[O:17])[N:10]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[C:9]3=[O:26])=[CH:27][CH:28]=1)#[N:2]