三乙胺 → (+/-)-[[[2,6-Bis(1-methylethyl)phenyl]amino]2-oxoethyl]-(phenylmethyl)phosphoramidic Acid, Nonyl Phenyl Ester

HRID 247828笔记

反应方程式

HRID 247828 反应方程式
[P:1](Cl)(Cl)([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:2].C(N(CC)CC)C.[CH2:19]([OH:28])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH3:29][CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:40])[CH3:39])[C:33]=1[NH:41][C:42](=[O:52])[CH2:43][NH:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH3:31]>C1(C)C=CC=CC=1>[CH3:31][CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:39])[CH3:40])[C:33]=1[NH:41][C:42](=[O:52])[CH2:43][N:44]([CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[P:1](=[O:2])([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[O:28][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:29]

参与物

6

反应物 4

HCID 8471三乙胺2 次HCID 89141-壬醇HCID 13038二氯磷酸苯酯HCID 19764427N-[2,6-bis(1-methylethyl)phenyl]-2-[phenylmethyl]amino-acetamide

产物 1

HCID 86746783(+/-)-[[[2,6-Bis(1-methylethyl)phenyl]amino]2-oxoethyl]-(phenylmethyl)phosphoramidic Acid, Nonyl Phenyl Ester收率 31.3%

试剂、催化剂与溶剂 1

HCID 1140甲苯溶剂2 次

实验过程

To an ice-cooled solution of phenyl dichlorophosphate (2.83 g, 0.02 mol) in dry toluene (50 mL) is added triethylamine (2.02 g, 0.02 mol) followed by nonyl alcohol (2.89 g, 0.02 mol) in dry toluene (40 mL) dropwise. The reaction mixture is stirred in an ice bath for 2 hours and then filtered. To this filtrate are added triethylamine (2.02 g, 0.02 mol) and a solution of N-[2,6-bis(1-methylethyl)phenyl]-2-[phenylmethyl]amino-acetamide (Example V) (6.40 g, 0.02 mole) and the mixture is stirred at room temperature overnight. The reaction mixture is filtered and concentrated. Flash column chromatography and crystallization from ethyl acetate affords 3.8 g of the title compound; IR (KBr); 3285, 2961, 2925, 2858, 2367, 1684, and 1508. 1H NMR (250 MHz, DMSO)δ9.22 (1 H, s), 7.44-6.92 (13 H, m), 4.50-4.30 (2 H, m), 4.30-4.00 (2 H, m), 4.00-3.60 (2 H, m), 3.10-2.80 (2 H, m), 1.70-1.40 (2 H, m), 1.4-1.18 (12 H, m), 1.18-1.00 (12 H, d, J=7 Hz), 0.98-0.76 (3 H, m).

后处理

  1. filtrationfiltered
  2. filtrationThe reaction mixture is filtered
  3. concentrationconcentrated
  4. customFlash column chromatography and crystallization from ethyl acetate

来源与证据

ORD记录
ord-4686ccefd43947c99c2937b26ae79b6f
来源数据集
uspto-grants-1993_05
专利号
US05208224

反应笔记

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