HRID20422

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7498

alpha-Bromotoluene

C7H7Br

HCID24758

Sodium hydride

HNa

HCID25517

未命名化合物

结构：CC(C)(C)OC(=O)N1[C@@H]([C@@H](O)[C@H](Cc2cc(F)cc(F)c2)N(Cc2ccccc2)Cc2ccccc2)COC1(C)C

HCID68561796

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1[C@@H]([C@@H](OCc2ccccc2)[C@H](Cc2cc(F)cc(F)c2)N(Cc2ccccc2)Cc2ccccc2)COC1(C)C

HCID68558039

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

Add sodium hydride (4.4 g, 110 mmol, 60% in mineral oil) portionwise to a room temperature maintained solution of (R)-4-[(1S,2S)-2-dibenzylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (50.5 g, 89.222 mmol) and benzyl bromide (22 mL, 184.96 mmol) in N,N-dimethylformamide (400 mL). Stir for 15 minutes and pour into saturated aqueous ammonium chloride. Extract with ethyl acetate, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 2:98 to 4:96 ethyl acetate:hexanes) to give the title compound as a viscous oil that solidifies upon standing (48.5 g, 83%).

WORKUP

后处理

extractionExtract with ethyl acetate
dry with materialdry (magnesium sulfate)
filtrationfilter
concentrationconcentrate
custompurify
wash(silica gel chromatography, eluting with 2:98 to 4:96 ethyl acetate:hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-253a4d6fd275467baf4d51ef47b51a8f
来源数据集: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07745438B2
来源说明: uspto-grants-2010_06

反应 SMILES

[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[C@@H:14]([C@@H:15]([OH:41])[C@@H:16]([N:26]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:17][C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[CH2:13][O:12][C:11]1([CH3:43])[CH3:42])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:44](Br)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[Cl-].[NH4+]>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[C@@H:14]([C@@H:15]([O:41][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C@@H:16]([N:26]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:17][C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[CH2:13][O:12][C:11]1([CH3:43])[CH3:42])=[O:9])([CH3:6])([CH3:4])[CH3:5]