Dichloromethane → HCID 18717979, compound

HRID 840618Notes

Reaction equation

HRID 840618 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH2:5][C:6]1[NH:7][CH:8]=[N:9][C:10]=1[Cl:11].C(N(CC)C(C)C)(C)C.ClCCl.[CH3:25][Si:26]([CH3:33])([CH3:32])[CH2:27][CH2:28][O:29][CH2:30]Cl>C(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH2:5][C:6]1[N:7]([CH2:30][O:29][CH2:28][CH2:27][Si:26]([CH3:33])([CH3:32])[CH3:25])[CH:8]=[N:9][C:10]=1[Cl:11]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 18717980HCID 18717980, compound

Product 1

HCID 18717979HCID 18717979, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 0.40 g of 3-(5-chloro-3H-imidazol-4-yl)-propionic acid methyl ester, 0.5 mL of N,N-diisopropylethylamine, 15 mL of dichloromethane and 0.4 mL of 2-(trimethylsilyl)ethoxymethyl chloride was stirred at room temperature for 24 h. The reaction mixture was diluted with 50 mL chloroform and 10 mL saturated aqueous Na2CO3 and the layers separated. The aqueous layer was extracted with 2×25 mL of chloroform and the combined organic layers dried over magnesium sulfate and concentrated under reduced pressure. Purification by chromatography eluting with ethyl acetate gave 0.8 g of 3-[5-chloro-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-propionic acid methyl ester as an oil.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with 2×25 mL of chloroform
  3. dry with materialthe combined organic layers dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-393bf6608ad548cea04d30214faa3b38
Source dataset
uspto-grants-2002_04
Patent number
US06369076B1

Reaction notes

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