HRID660396

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COCCCn1ncc2ccc(C[C@@H](C[C@H](NC(=O)OC(C)(C)C)C(O)C[C@H](COCc3ccccc3)C(C)C)C(C)C)cc21

HCID59630979

未命名化合物

PRODUCTS

生成物

结构：COCCCn1ncc2ccc(C[C@@H](C[C@H](NC(=O)OC(C)(C)C)[C@@H](O)C[C@H](CO)C(C)C)C(C)C)cc21

HCID59630975

未命名化合物

收率 30%

HCID59630990

未命名化合物

收率 14%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID9942167

Palladium hydroxide

H2O2Pd

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

To a solution of tert-butyl (3S,5S,8S)-8-(benzyloxymethyl)-6-hydroxy-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamate (1.3 g, 2.1 mmol) in methanol 30 mL) was added 20% Pd(OH)2/C (26 mg). The mixture was hydrogenated under a balloon of H2 at rt overnight and filtered. The filtrate was evaporated and purified by preparative HPLC to give tert-butyl (3S,5S,6S,8S)-6-hydroxy-8-(hydroxymethyl)-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamate (0.33 g, 30% yield) as an oil and tert-butyl (3S,5S,6R,8S)-6-hydroxy-8-(hydroxymethyl)-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamate (0.15 g, 14%) as an oil. MS: 534 (M++1)

WORKUP

后处理

filtrationfiltered
customThe filtrate was evaporated
custompurified by preparative HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-90d61042f4e948fe8a94dc9d62f49f2a
来源数据集: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08084485B2
来源说明: uspto-grants-2011_12

反应 SMILES

C([O:8][CH2:9][C@H:10]([CH:43]([CH3:45])[CH3:44])[CH2:11][CH:12]([OH:42])[C@@H:13]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:14][C@H:15]([CH2:19][C:20]1[CH:28]=[C:27]2[C:23]([CH:24]=[N:25][N:26]2[CH2:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:22][CH:21]=1)[CH:16]([CH3:18])[CH3:17])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[OH:42][C@@H:12]([CH2:11][C@H:10]([CH2:9][OH:8])[CH:43]([CH3:45])[CH3:44])[C@@H:13]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40])[CH2:14][C@H:15]([CH2:19][C:20]1[CH:28]=[C:27]2[C:23]([CH:24]=[N:25][N:26]2[CH2:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:22][CH:21]=1)[CH:16]([CH3:17])[CH3:18].[OH:42][C@H:12]([CH2:11][C@H:10]([CH2:9][OH:8])[CH:43]([CH3:45])[CH3:44])[C@@H:13]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40])[CH2:14][C@H:15]([CH2:19][C:20]1[CH:28]=[C:27]2[C:23]([CH:24]=[N:25][N:26]2[CH2:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:22][CH:21]=1)[CH:16]([CH3:17])[CH3:18]