Triethylamine → HCID 54311265, compound

HRID 1755980Notes

Reaction equation

HRID 1755980 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][CH:12]2[CH2:17][CH2:16][C:15]3([CH3:18])[C:13]2([C:19](O)=[O:20])[CH2:14]3)[N:4]=1.C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O.[NH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37]>ClCCl>[CH3:39][O:38][C:36]([CH2:35][NH:34][C:19]([C:13]12[CH2:14][C:15]1([CH3:18])[CH2:16][CH2:17][CH:12]2[O:11][C:5]1[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[N:6]=1)=[O:20])=[O:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 69221Glycine methyl esterHCID 19392067HCID 19392067, compound

Product 1

HCID 54311265HCID 54311265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1 g (3.4 mmol) of 2-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-5-methyl-bicyclo[3.1.0]hexane-1-carboxylic acid is dissolved in 50 ml of dichloromethane and mixed with 2.1 g of triethylamine. 0.53 g (3.4 mmol) of phosphorus oxychloride, dissolved in 5 ml of dichloromethane, is added dropwise at -5° C. and the mixture is subsequently stirred for 5 minutes. A solution of 0.9 g (7.1 mmol) of methyl aminoacetate (glycine methyl ester) in 5 ml of dichloromethane is then added, with continued stirring, to the solution of the acid chloride. The reaction mixture is then allowed to reach room temperature within the space of 15 minutes. Subsequently, the organic phase is separated off, washed three times with water, dried over magnesium sulphate and evaporated. The remaining residue is purified by means of (flash) chromatography. 2-(4,6-Dimethoxy-pyrimidin-2-yl-oxy)-5-methyl-bicyclo-[3.1.0]hexane-1-carboxylic acid N-(methoxycarbonyl-methyl)-amide is obtained in the form of an oil.

Workup

  1. additionis added dropwise at -5° C.
  2. customto reach room temperature within the space of 15 minutes
  3. customSubsequently, the organic phase is separated off
  4. washwashed three times with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe remaining residue is purified by means of (flash) chromatography

Sources & evidence

ORD record
ord-517ba6ab590f4ff48b0c2367347ab0a9
Source dataset
uspto-grants-1995_08
Patent number
US05439874

Reaction notes

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