Pyridine → HCID 13649258, compound

HRID 1200155Notes

Reaction equation

HRID 1200155 reaction equation
[CH3:1][C:2]([NH:10][C:11](=[O:29])[C@@H:12]([NH2:28])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl>[CH3:9][C:2]([NH:10][C:11](=[O:29])[C@@H:12]([NH:28][C:36](=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])([CH3:1])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 14696302HCID 14696302, compound

Product 1

HCID 13649258HCID 13649258, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 80 ml of a methylene chloride solution containing 2.14 g of (2S)-N-(α,α-dimethylbenzyl)-2-amino-6-(benzyloxycarbonylamino)hexanamide (prepared as described in Preparation 9) and 0.51 g of pyridine were added dropwise, whilst ice-cooling, 30 ml of a methylene chloride solution containing 0.76 g benzoyl chloride, over a period of 10 minutes, with stirring. The mixed solution was stirred for a further 1.5 hours at room temperature, and then the solvent was distilled off. The residue was dissolved in ethyl acetate containing a small amount of water. A 10% w/v aqueous solution of citric acid was added, and then the solution was extracted with ethyl acetate. The extract was washed with a 5% w/v aqueous solution of sodium bicarbonate and then with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel column chromatography. The fraction eluted with a 1:1 by volume mixture of ethyl acetate and hexane gave 2.06 g of the title compound as an amorphous substance melting at 53°-58° C. (with decomposition)

Workup

  1. additionwere added dropwise, whilst ice-
  2. temperaturecooling
  3. stirringThe mixed solution was stirred for a further 1.5 hours at room temperature
  4. distillationthe solvent was distilled off
  5. dissolutionThe residue was dissolved in ethyl acetate containing a small amount of water
  6. additionwas added
  7. extractionthe solution was extracted with ethyl acetate
  8. washThe extract was washed with a 5% w/v aqueous solution of sodium bicarbonate
  9. dry with materialwith a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. washThe fraction eluted with a 1:1 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-aa514f5fd0c94c0e83fec209942545e4
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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