1-Hydroxybenzotriazole → N-[[1-[[(Phenylmethoxy)carbonyl]amino]cyclohexyl]carbonyl]-L-valinol

HRID 1627465Notes

Reaction equation

HRID 1627465 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[C:13]1([CH2:19][O:20][C:21]([NH:23][C:24]2([C:30]([OH:32])=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.ON1C2C=CC=CC=2N=N1.[NH2:43][C@H:44]([CH2:48][OH:49])[CH:45]([CH3:47])[CH3:46]>C(Cl)Cl>[C:13]1([CH2:19][O:20][C:21]([NH:23][C:24]2([C:30]([NH:43][C@H:44]([CH2:48][OH:49])[CH:45]([CH3:47])[CH3:46])=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)=[O:22])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 640993L-ValinolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 113578861-(Cbz-amino)cyclohexanecarboxylic acid

Product 1

HCID 24875999N-[[1-[[(Phenylmethoxy)carbonyl]amino]cyclohexyl]carbonyl]-L-valinolYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After 422 mg (2.2 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 555 mg (2 mmol) of 1-[[(phenylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid, 322 mg (2.1 mmol) of 1-hydroxybenzotriazole and 206 mg (2 mmol) of L-valinol in 20 ml of methylene chloride under ice-cooling, the mixture was stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure, ethyl acetate was added to the residue, and the mixture was washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 662 mg (91%) of the title compound.

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure, ethyl acetate
  3. additionwas added to the residue
  4. washthe mixture was washed with water
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-818a3ca562674e48a958b83b66f82b18
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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