HRID1013542

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81531

Diisopropylethylamine

C8H19N

结构：CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[P-](F)(F)(F)(F)F

HCID151348

Tri(dimethylamino)benzotriazol-1-yloxyphosphonium hexafluorophosphate

C12H22F6N6OP2

HCID516892

Sodium Bicarbonate

CHNaO3

HCID57717474

tert-Butyl [2-amino-4-(thiophen-2-yl)phenyl]carbamate

C15H18N2O2S

HCID57925907

未命名化合物

PRODUCTS

生成物

结构：CCOP(C)(=O)CCC(=O)c1ccc(C(=O)Nc2cc(-c3cccs3)ccc2NC(=O)OC(C)(C)C)cc1

HCID57925974

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

4-{3-[(ethyloxy)(methyl)phosphoryl]propanoyl}benzoic acid (1 g, 3.52 mmol), 1,1-dimethylethyl [2-amino-4-(2-thienyl)phenyl]carbamate (1.532 g, 5.28 mmol), DIPEA (0.922 mL, 5.28 mmol) and BOP (2.334 g, 5.28 mmol) were stirred in DMF (10 mL) at room temperature overnight. Saturated NaHCO3 was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with water and brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by MPLC (0-20% MeOH-EtOAc) gave ethyl {3-[4-({[2-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]-3-oxopropyl}methylphosphinate as an orange solid. MS: cal'd 457 (MH+-Boc), exp 457 (MH+-Boc).

WORKUP

后处理

extractionthe products extracted into EtOAc (×2)
washThe combined organic extracts were washed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customPurification of the residue by MPLC (0-20% MeOH-EtOAc)
customgave ethyl {3-[4-({[2-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]-3-oxopropyl}methylphosphinate as an orange solid

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-91c96a510e38439fac28de83780b889e
来源数据集: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07981874B2
来源说明: uspto-grants-2011_07

反应 SMILES

[CH2:1]([O:3][P:4]([CH2:7][CH2:8][C:9]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)=[O:10])([CH3:6])=[O:5])[CH3:2].[NH2:20][C:21]1[CH:26]=[C:25]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)[CH:24]=[CH:23][C:22]=1[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:38][C:35]([O:34][C:33]([NH:32][C:22]1[CH:23]=[CH:24][C:25]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)=[CH:26][C:21]=1[NH:20][C:15]([C:14]1[CH:13]=[CH:12][C:11]([C:9](=[O:10])[CH2:8][CH2:7][P:4]([CH3:6])(=[O:5])[O:3][CH2:1][CH3:2])=[CH:19][CH:18]=1)=[O:17])=[O:39])([CH3:36])[CH3:37]