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

HRID 1698438Notes

Reaction equation

HRID 1698438 reaction equation
[CH2:1]([NH:5][C:6](=[O:15])[C@@H:7]([OH:14])[C@@H:8]([NH2:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH2:2][CH2:3][CH3:4].[N:16]1([C:22]([NH:24][C:25]2([C:31](O)=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>ClCCl>[OH:14][C@@H:7]([C@@H:8]([NH:13][C:31]([C:25]1([NH:24][C:22]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:23])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)=[O:32])[CH2:9][CH2:10][CH2:11][CH3:12])[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:15]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 115071371-(Morpholine-4-carboxamido)cyclohexanecarboxylic acidHCID 59655570(2S,3S)-N-butyl-3-amino-2-hydroxyheptanamide

Product 1

HCID 53630496N-[(2S,3S)-2-hydroxy-1-[N-(butyl)amino]-1-oxo-3-heptyl]-1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In anhydrous dichloromethane were dissolved 254 mg (1.21 mmol) of (2S,3S)-N-butyl-3-amino-2-hydroxyheptanamide, 310 mg (1.21 mmol) of 1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxylic acid and 230 mg (1.45 mmol) of 1-hydroxy-benzotriazole, subsequently, under nitrogen stream, 278 mg (1.45 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide was added to the solution 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 489 mg (Yield: 89%) 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-6535c5576432457e9b6c783bead67816
Source dataset
uspto-grants-2012_04
Patent number
US08163943B2

Reaction notes

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