戴斯-马丁氧化剂 → 3-(11-tert-Butoxycarbonylamino-undecanoylamino)-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

HRID 2075813笔记

反应方程式

HRID 2075813 反应方程式
[C:1]([O:5][C:6](=[O:44])[CH2:7][CH:8]([NH:23][C:24](=[O:43])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH:9]([OH:22])[CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:44])[CH2:7][CH:8]([NH:23][C:24](=[O:43])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:9](=[O:22])[CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])([CH3:4])([CH3:2])[CH3:3]

参与物

5

反应物 3

HCID 159087戴斯-马丁氧化剂HCID 516892碳酸氢钠HCID 866130763-(11-tert-Butoxycarbonylamino-undecanoylamino)-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

产物 1

HCID 866130773-(11-tert-Butoxycarbonylamino-undecanoylamino)-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester收率 64%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

Composition 15 (56 mg, 0.088 mmol) and Dess-Martin periodinane (48 mg, 0.114 mmol, 1.3 equiv) in DCM (2 mL) were added to a dry round bottom flask equipped with a magnetic stir bar. The cloudy white suspension was allowed to react for 20 minutes. Saturated NaHCO3 (20 ml) was added and the reaction was extracted with EtOAc (20 mL). The organic layer was dried over NaHCO3, concentrated in vacuo, and purified via column chromatography (silica gel, 1:1, hexanes/EtOAc) to give 16 (23 mg, 0.036 mmol, 64% yield) as a sticky white solid. ESMS: 635.4 (M+H+), 657.2 (M+Na+).

后处理

  1. customequipped with a magnetic stir bar
  2. customto react for 20 minutes
  3. extractionthe reaction was extracted with EtOAc (20 mL)
  4. dry with materialThe organic layer was dried over NaHCO3
  5. concentrationconcentrated in vacuo
  6. custompurified via column chromatography (silica gel, 1:1, hexanes/EtOAc)

来源与证据

ORD记录
ord-eab68077bacf4a509235d588d57d259b
来源数据集
uspto-grants-2011_04
专利号
US07923433B2

反应笔记

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