1-Octanol → HCID 67653950, compound

HRID 1459443Notes

Reaction equation

HRID 1459443 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:10]([O:17][C:18]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:31][C:19]=1[C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](Cl)=[O:29])=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1>C(#N)C.CCOCC>[CH2:10]([O:17][C:18]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[CH:31][C:19]=1[C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:29])=[O:21])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 9571-OctanolHCID 1049PyridineHCID 86751842HCID 86751842, compound

Product 1

HCID 67653950HCID 67653950, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

0.66 g (5 mmol) of 1-octanol was dropwise added to the solution of 1.5 g (3.2 mmol) of 6-{N-[2,5-di(benzyloxy)benzoyl]amino}hexanoyl chloride in 15 ml of anhydrous acetonitrile and 0.29 g (3.7 mmol) of anhydrous pyridine during 5 minutes under cooling and stirring at 0°-5° C. The reaction mixture was stirred at room temperature for 10 hours, then evaporated under reduced pressure to dryness at a temperature below 50° C. The residue obtained was dissolved in 40 ml of ether and was successively washed with water, 2% sodium hydroxide solution and finally with water, then dried and evaporated under reduced pressure. The residue was purified on a silicagel column by using ethyl acetate as eluent to give 0.96 g (54%) of the aimed compound, m.p.: 48°-50° C.

Workup

  1. temperatureunder cooling
  2. stirringThe reaction mixture was stirred at room temperature for 10 hours
  3. customevaporated under reduced pressure to dryness at a temperature below 50° C
  4. customThe residue obtained
  5. washwas successively washed with water, 2% sodium hydroxide solution and finally with water
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was purified on a silicagel column

Sources & evidence

ORD record
ord-c040cbde056846df9b6c15c081a99330
Source dataset
uspto-grants-1998_12
Patent number
US05854250

Reaction notes

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