Diethylene Glycol Monoethyl Ether → HCID 86754516, compound

HRID 618810Notes

Reaction equation

HRID 618810 reaction equation
[CH2:1]([C:3]1([CH2:24][CH3:25])[CH2:12][CH:11]([CH2:13][CH2:14][S:15]([NH:18][CH2:19][C:20]([OH:22])=[O:21])(=[O:17])=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:23])[CH:9]=2)[O:4]1)[CH3:2].[CH2:26]([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33]O)[CH3:27].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:24]([C:3]1([CH2:1][CH3:2])[CH2:12][CH:11]([CH2:13][CH2:14][S:15]([NH:18][CH2:19][C:20]([O:22][CH2:27][CH2:26][O:28][CH2:29][CH2:30][O:31][CH2:32][CH3:33])=[O:21])(=[O:17])=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:23])[CH:9]=2)[O:4]1)[CH3:25]

Participants

6

Reactant 3

HCID 8146Diethylene Glycol Monoethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 67597722HCID 67597722, compound

Product 1

HCID 86754516HCID 86754516, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.5 g (1.35 mmol) of [(2,2-diethyl-6-methylchroman-4-yl)ethylsulfonylamino]acetic acid, 0.2 g (1.5 mmol) of diethylene glycol monoethyl ether, 0.31 g (1.5 mmol) of DCC and 2 mg (0.01 mmol) of DMAP in 7 ml of methylene chloride is stirred overnight at RT. It is washed successively with 5% strength acetic acid, saturated sodium bicarbonate solution and water, dried over magnesium sulfate and concentrated in vacuo. After subsequent purification by chromatography using cyclohexane/EA 4:1, 0.29 g of 2-(2-ethoxyethoxy)ethyl [(2,2-diethyl-6-methylchroman-4-yl)ethylsulfonylamino]acetate is obtained as a viscous oil.

Workup

  1. washIt is washed successively with 5% strength acetic acid, saturated sodium bicarbonate solution and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customAfter subsequent purification by chromatography

Sources & evidence

ORD record
ord-c4eac2dae751420b98c3f0c4321eda5d
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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