1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[(2S,3S)-2-hydroxy-1-[N-[(3,4-methylenedioxy)phenyl]amino]-1-oxo-3-heptyl]-1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxamide

HRID 2053475Notes

Reaction equation

HRID 2053475 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:10][C:11](=[O:20])[C@@H:12]([OH:19])[C@@H:13]([NH2:18])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=2[O:2]1.[N:21]1([C:27]([NH:29][C:30]2([C:36](O)=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>ClCCl>[OH:19][C@@H:12]([C@@H:13]([NH:18][C:36]([C:30]1([NH:29][C:27]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:28])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1)=[O:37])[CH2:14][CH2:15][CH2:16][CH3:17])[C:11]([NH:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)=[O:20]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 115071371-(Morpholine-4-carboxamido)cyclohexanecarboxylic acidHCID 59655569(2S,3S)-N-[(3,4-methylenedioxy)phenyl]-3-amino-2-hydroxyheptanamide

Product 1

HCID 53630495N-[(2S,3S)-2-hydroxy-1-[N-[(3,4-methylenedioxy)phenyl]amino]-1-oxo-3-heptyl]-1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In anhydrous dichloromethane were dissolved 344 mg (1.23 mmol) of (2S,3S)-N-[(3,4-methylenedioxy)phenyl]-3-amino-2-hydroxyheptanamide, 315 mg (1.23 mmol) of 1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxylic acid and 233 mg (1.48 mmol) of 1-hydroxybenzotriazole, and then, under nitrogen stream, 284 mg (1.48 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide was added to the above mixture at 0° C. Thereafter, the temperature of the reaction mixture was returned to room temperature, and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in 80 ml of ethyl acetate, and the resulting mixture was washed successively with water, a 10% aqueous potassium hydrogen sulfate solution, a saturated aqueous sodium hydrogen carbonate solution and a saturated NaCl solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 574 mg (Yield: 90%) of the desired compound.

Workup

  1. customwas returned to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 80 ml of ethyl acetate
  4. washthe resulting mixture was washed successively with water
  5. dry with materiala 10% aqueous potassium hydrogen sulfate solution, a saturated aqueous sodium hydrogen carbonate solution and a saturated NaCl solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-93feae36715547a582445329b248a153
Source dataset
uspto-grants-2008_02
Patent number
US07326799B2

Reaction notes

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