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

HRID 1953442Notes

Reaction equation

HRID 1953442 reaction equation
[N:1]1([C:7]([NH:9][C:10]2([C:16]([OH:18])=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:19][C:20]([NH:23][C:24](=[O:33])[CH:25]([OH:32])[C@@H:26]([NH2:31])[CH2:27][CH2:28][CH2:29][CH3:30])([CH3:22])[CH3:21].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>C(Cl)Cl.C(OCC)(=O)C>[OH:32][CH:25]([C@@H:26]([NH:31][C:16]([C:10]1([NH:9][C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)=[O:8])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:18])[CH2:27][CH2:28][CH2:29][CH3:30])[C:24]([NH:23][C:20]([CH3:19])([CH3:21])[CH3:22])=[O:33]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 115071371-(Morpholine-4-carboxamido)cyclohexanecarboxylic acidHCID 21971170HCID 21971170, compound

Product 1

HCID 11496204N-[(2RS,3S)-2-hydroxy-1-[N-(2-methyl-2-propyl)amino]-1-oxo-3-heptyl]-1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxamideYield 61.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.26 g (1.26 mmol) of 1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxylic acid (1.26 mmol), 0.27 g (1.26 mmol) of (2RS,3S)-N-(2-methyl-2-propyl)-3-amino-2-hydroxyheptanamide and 0.24 g (1.5 mmol) of 1-hydroxybenzotriazole were dissolved in 15 ml of anhydrous methylen chloride and then, under air current of nitrogen, 0.29 g (1.5 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide was added thereto at 0° C. Thereafter, the reaction solution was warmed to the room temperature and stirred overnight. The reaction solution was concentrated under reduced condition. The residue thus obtained was dissolved in 100 ml of ethyl acetate and washed successively with water, aqueous solution of 10% potassium hydrogensulfate, aqueous solution of saturated sodium hydrogencarbonte and saturated brine. After drying over anhydrous magnesium sulfate, the reaction mixture was concentrated under reduced pressure. The residue was separated out with the silicagel column chromatography, whereby 0.35 g of N-[(2RS,3S)-2-hydroxy-1-[N-(2-methyl-2-propyl)amino]-1-oxo-3-heptyl]-1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxamide was obtained.

Workup

  1. customat 0° C
  2. concentrationThe reaction solution was concentrated under reduced condition
  3. customThe residue thus obtained
  4. washwashed successively with water, aqueous solution of 10% potassium hydrogensulfate, aqueous solution of saturated sodium hydrogencarbonte and saturated brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. customThe residue was separated out with the silicagel column chromatography

Sources & evidence

ORD record
ord-b4ffb5f7994a4c6489eaf6d2f49e4865
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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