1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → n-t-Butoxy-3-(4-methoxyphenylthio)propionamide

HRID 380076Notes

Reaction equation

HRID 380076 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:5][CH:4]=1.Cl.[C:16]([O:20][NH2:21])([CH3:19])([CH3:18])[CH3:17].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C=O)C.O.C(OCC)(=O)C.C(N(CC)CC)C>[C:16]([O:20][NH:21][C:12](=[O:14])[CH2:11][CH2:10][S:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

9

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 44314443-[(4-methoxyphenyl)thio]propanoic acid

Product 1

HCID 18368974n-t-Butoxy-3-(4-methoxyphenylthio)propionamideYield 101.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound prepared in Example 8(11) (1.00 g) in DMF (20 ml), t-butoxyamine hydrochloride (652 mg), triethylamine (0.8 ml), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC) hydrochloride (995 mg) and 1-hydroxybenzotriazole (HOBt) hydrate (795 mg) were added at 0° C. The mixture was stirred for 16 hours at room temperature. To the reaction mixture, ethyl acetate and water were added. The organic phase was washed with 0.1 N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and concentrated to give the title compound (1.35 g) having the following physical data.

Workup

  1. washThe organic phase was washed with 0.1 N hydrochloric acid
  2. dry with materiala saturated aqueous solution of sodium bicarbonate, water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-33efd14f550a45b4b8960ac0440f2872
Source dataset
uspto-grants-2001_10
Patent number
US06300514B1

Reaction notes

Loading…