氢化钠 → 2-(Diethoxyphosphoryl)-3-cyclopropylproprionic acid 4-methoxybenzyl ester

HRID 8777

反应方程式

HRID 8777 反应方程式
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:23]=[CH:22][C:8]([CH2:9][O:10][C:11](=[O:21])[CH2:12][P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1.Br[CH2:25][CH:26]1[CH2:28][CH2:27]1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11](=[O:21])[CH:12]([P:13]([O:15][CH2:16][CH3:17])([O:18][CH2:19][CH3:20])=[O:14])[CH2:25][CH:26]2[CH2:28][CH2:27]2)=[CH:22][CH:23]=1

参与物

7

反应物 4

HCID 24758氢化钠HCID 81503溴甲基环丙烷HCID 516892碳酸氢钠HCID 540209272-(Diethoxyphosphoryl)acetic acid para-methoxybenzyl ester

产物 1

HCID 540841052-(Diethoxyphosphoryl)-3-cyclopropylproprionic acid 4-methoxybenzyl ester收率 60.9%

试剂、催化剂与溶剂 2

HCID 3283乙醚溶剂HCID 6228N,N-二甲基甲酰胺溶剂2 次

实验过程

To a suspension of 60% sodium hydride in mineral oil (0.840 g, 21.0 mmol) in DMF (100 mL) was added a solution of 2-(diethoxyphosphoryl)acetic acid 4-methoxybenzyl ester (6.04 g, 19.1 mmol) from Step A in DMF (10 mL). The reaction mixture was stirred for 30 min at room temperature. Bromomethylcyclopropane (2.4 mL, 24.8 mmol) was added and the reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with diethyl ether, poured into saturated sodium bicarbonate, and extracted three times with diethyl ether. The organic layers were combined, washed with saturated sodium chloride, dried over sodium sulfate, and filtered. The volatiles were removed in vacuo and the residue was purified by FC (40% ethyl acetate in hexanes) to afford 4.31 g of the title compound.

后处理

  1. stirringthe reaction mixture was stirred at room temperature for 12 h
  2. extractionextracted three times with diethyl ether
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe volatiles were removed in vacuo
  7. customthe residue was purified by FC (40% ethyl acetate in hexanes)

来源与证据

ORD记录
ord-e31142420d854a6b93bb0fdda233b4cb
来源数据集
uspto-grants-2006_08
专利号
US07091211B2

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