Triethylamine → N-[2-(tert-Butyldimethylsilanyloxymethyl)allyl]-2-diazo-N-(2,4-dimethoxybenzyl)acetamide

HRID 83574Notes

Reaction equation

HRID 83574 reaction equation
[Si:1]([O:8][CH2:9][C:10](=[CH2:24])[CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[O:22][CH3:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.O=C1CCC(=O)N1[O:39][C:40](=O)[CH:41]=[N+:42]=[N-:43]>C(Cl)(Cl)Cl>[Si:1]([O:8][CH2:9][C:10](=[CH2:24])[CH2:11][N:12]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[O:22][CH3:23])[C:40](=[O:39])[CH:41]=[N+:42]=[N-:43])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 713461412-Diazonio-1-[(2,5-dioxopyrrolidin-1-yl)oxy]ethen-1-olateHCID 89465872[2-(tert-Butyldimethylsilanyloxymethyl)allyl]-(2,4-dimethoxybenzyl)amine

Product 1

HCID 123927604N-[2-(tert-Butyldimethylsilanyloxymethyl)allyl]-2-diazo-N-(2,4-dimethoxybenzyl)acetamideYield 48.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of [2-(tert-butyldimethylsilanyloxymethyl)allyl]-(2,4-dimethoxybenzyl)amine (384 mg) in chloroform (3.8 ml) were sequentially added triethylamine (0.23 ml) and diazoacetic acid 2,5-dioxopyrrolidin-1-yl ester (200 mg) at room temperature, and the mixture was stirred for 16 hours. This reaction mixture was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1) to give the titled compound (223 mg).

Workup

  1. customat room temperature
  2. concentrationThis reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-bc3a10e3b8974dafafc051fea5b678ed
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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