HRID1852129

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID23665647

2-Methyl-2-propanol, potassium salt

C4H9KO

HCID70979100

未命名化合物

$结构：COC(=O)[C@@]12C[C@H]1/C=C\CCC(C)C[C@@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)N1C[C@H](O)C[C@H]1C(=O)N2$

HCID71005125

未命名化合物

PRODUCTS

生成物

$结构：COc1cnc(O[C@@H]2C[C@H]3C(=O)N[C@]4(C(=O)O)C[C@H]4/C=C\CCC(C)C[C@@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)N3C2)c2ccccc12$

HCID86683204

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID679

Dimethyl sulfoxide

C2H6OS

PROCEDURE

实验过程

To a mixture of (2R,6S,7R,13aS,14aR,16aS,Z)-methyl 6-((tert-butoxycarbonyl)amino)-2-hydroxy-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (152 mg, 0.3 mmol),1-fluoro-4-methoxyisoquinoline (128 mg, 0.720 mmol), and t-BuOK (168 mg, 1.500 mmol) was added DMSO (5 mL) and then sonicated for 15 min. The resulting solution was stirred for 4 h. The reaction was quenched with water, acidified with 6 N HCl, extracted with EtOAc, washed with brine, dried over MgSO4. After concentration, the residue (2R,6S,7R,13aS,14aR,16aS,Z)-6-((tert-butoxycarbonyl)amino)-2-((4-methoxyisoquinolin-1-yl)oxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylic acid was obtained as a solid (150 mg) that will be used as it is. LC/MS: MS m/z (M+H)+ 651.23.

WORKUP

后处理

customsonicated for 15 min
customThe reaction was quenched with water
extractionextracted with EtOAc
washwashed with brine
dry with materialdried over MgSO4
concentrationAfter concentration

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-41a86df7570c41febba4132b79ee45d7
来源数据集: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08957203B2
来源说明: uspto-grants-2015_02

反应 SMILES

[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([OH:28])[CH2:27][C@H:21]2[C:20](=[O:29])[NH:19][C@:18]2([C:31]([O:33]C)=[O:32])[CH2:30][C@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][CH:12]([CH3:35])[CH2:11][C@H:10]1[CH3:36])=[O:7])([CH3:4])([CH3:3])[CH3:2].F[C:38]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:41]([O:48][CH3:49])=[CH:40][N:39]=1.CC([O-])(C)C.[K+]>CS(C)=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:38]3[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:41]([O:48][CH3:49])=[CH:40][N:39]=3)[CH2:27][C@H:21]2[C:20](=[O:29])[NH:19][C@:18]2([C:31]([OH:33])=[O:32])[CH2:30][C@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][CH:12]([CH3:35])[CH2:11][C@H:10]1[CH3:36])=[O:7])([CH3:3])([CH3:4])[CH3:2]