1-Hydroxybenzotriazole → HCID 56986282, compound

HRID 1953439Notes

Reaction equation

HRID 1953439 reaction equation
[NH2:1][C@@H:2]([CH2:15][CH2:16][CH2:17][CH3:18])[CH:3]([OH:14])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[N:19]1([C:25]([NH:27][C:28]2([C:34](O)=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[OH:14][CH:3]([C@@H:2]([NH:1][C:34]([C:28]1([NH:27][C:25]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:26])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1)=[O:35])[CH2:15][CH2:16][CH2:17][CH3:18])[C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:5]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 115071371-(Morpholine-4-carboxamido)cyclohexanecarboxylic acidHCID 56995658phenylmethyl (2RS,3S)-3-amino-2-hydroxyheptanoate

Product 1

HCID 56986282HCID 56986282, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Subsequently, under ice-cooled condition, to 9.3 g (37 mmol) of phenylmethyl (2RS,3S)-3-amino-2-hydroxyheptanoate, 9.5 g (37 mmol) of 1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxylic acid synthesized in Reference Example 5 and 6.0 g (45 mmol) of 1-hydroxybenzotriazole in 100 ml of dichloromethane, 8.5 g (45 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added and then was stirred at the room temperature for 18 hours. The reaction solution was concentrated under reduced pressure. The residue was washed successively with water, aqueous solution of 10% of potassium hydrogensulfate, aqueous solution of saturated sodium hydrogen-carbonate and saturated brine in addition of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled away from the reaction mixture under reduced pressure. The residue was purified by the silicagel column chromatography, whereby 16.8 g of phenylmethyl (2RS,3S)-2-hydroxy-3-[N-[1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarbonyl]amino]heptanoate was obtained.

Workup

  1. temperatureSubsequently, under ice-cooled condition
  2. additionwas added
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. washThe residue was washed successively with water, aqueous solution of 10% of potassium hydrogensulfate, aqueous solution of saturated sodium hydrogen-carbonate and saturated brine in addition of ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled away from the reaction mixture under reduced pressure
  7. customThe residue was purified by the silicagel column chromatography

Sources & evidence

ORD record
ord-38974ea77c63457aba03e22c4bedf1fd
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

Loading…