Acetonitrile → HCID 178445940, compound

HRID 1769436Notes

Reaction equation

HRID 1769436 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[C@H:10]([CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)[NH:11][C:12](=[O:19])[C@H:13]([CH2:15][CH:16]([CH3:18])[CH3:17])[NH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31]1([CH2:41][CH2:42][CH:43]=O)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1.[P:45]([O-])([O:54]CC1C=CC=CC=1)[O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C(#N)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:30])[C@H:10]([CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)[NH:11][C:12](=[O:19])[C@H:13]([CH2:15][CH:16]([CH3:17])[CH3:18])[NH:14][C:43](=[P:45]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:54])[CH2:42][CH2:41][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 110414091-NaphthalenepropanalHCID 15199902L-leucyl-L-tryptophan benzyl esterHCID 21904359Dibenzylphosphite

Product 1

HCID 178445940HCID 178445940, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of L-leucyl-L-tryptophan benzyl ester (408 mg) and 3-(1-naphthyl)propionaldehyde (220 mg) in toluene (10 ml) was heated to reflux in a Dean-Stark apparatus for 2 hours. After cooling, dibenzyl phosphite (252 mg) and acetonitrile (10 ml) were added to the mixture and the resulting solution was stirred at 100° C. for 16 hours. After being cooled to room temperature, the mixture was concentrated under reduced pressure. The residue was separated and purified by silica gel chromatography (chloroform:ethyl acetate=5:1) to give two diastereomers of the title compound as colorless oil (a: 58 mg, b: 95 mg).

Workup

  1. temperaturewas heated
  2. temperatureto reflux in a Dean-Stark apparatus for 2 hours
  3. temperatureAfter cooling
  4. temperatureAfter being cooled to room temperature
  5. concentrationthe mixture was concentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified by silica gel chromatography (chloroform:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-a2fe93a780e84d09851c811468f21b05
Source dataset
uspto-grants-1995_01
Patent number
US05380921

Reaction notes

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