HRID1825036

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8739

Carzenide

C7H7NO4S

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

结构：CC(C)(C)OC(=O)N1CCC(NC(=O)OCc2ccccc2)C(N)C1

HCID22143118

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1CC[C@H](NC(=O)OCc2ccccc2)[C@H](NC(=O)c2ccc(S(N)(=O)=O)cc2)C1

HCID86587040

未命名化合物

收率 45.9%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

1-tert-butoxycarbonyl-3-amino-4-(benzyloxycarbonyl)amino-piperidine (151b) (300 mg) was dissolved in DMF (5 mL) prior to addition of Hunig's base (0.45 mL). 4-(aminosulfonyl)benzoic acid (210 mg) was added followed by BOP (420 mg). The solution was stirred for 8 h then quenched with aqueous NH4Cl. The mixture was partitioned between EtOAc and water. The organic layer was washed with NaHCO3, 5% LiCl (3×), and brine. The organic layer was dried, filtered, and concentrated. Flash chromatography of the residue provided tert-butyl (cis)-3-{[4-(aminosulfonyl)benzoyl]amino}-4-{[(benzyloxy)carbonyl]amino}-1-piperidinecarboxylate (210 mg). MS found: (M−H)−=531.3.

WORKUP

后处理

customthen quenched with aqueous NH4Cl
customThe mixture was partitioned between EtOAc and water
washThe organic layer was washed with NaHCO3, 5% LiCl (3×), and brine
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ba88124e1e694a01900adf8968c55647
来源数据集: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07045521B2
来源说明: uspto-grants-2006_05

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH:10]([NH2:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[NH2:35][S:36]([C:39]1[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=1)(=[O:38])=[O:37].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[NH2:35][S:36]([C:39]1[CH:40]=[CH:41][C:42]([C:43]([NH:25][C@H:10]2[C@@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]2)=[O:44])=[CH:46][CH:47]=1)(=[O:37])=[O:38]