Acetic Acid → HCID 131718931, compound

HRID 1609362Notes

Reaction equation

HRID 1609362 reaction equation
[NH:1]([C:19]([O:21]CC1C=CC=CC=1)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([CH2:17][F:18])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Br.[C:30](O)(=O)[CH3:31]>>[NH:1]([C:19]([CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][CH2:30][CH3:31])=[O:21])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([CH2:17][F:18])=[O:16])[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:8])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 131718932HCID 131718932, compound

Product 1

HCID 131718931HCID 131718931, compoundYield 52%

Procedure

The Z-Leu-Leu-CH2F (0.39 g) obtained in Example 3 was dissolved in acetic acid (5 ml) including a 25% anhydrous hydrogen bromide and the mixture was agitated at room temperature for 3 hours. After the end of the reaction, the solvent was distilled off and the resultant residue was dissolved in anhydrous methylene chloride (5 ml). To this, under ice water, were added triethylamine (0.23 g) and octanoylchloride (0.2 g) to dissolve it, then this was washed with a 10% aqueous citric acid solution, a 5% sodium hydrogencarbonate, then a saturated saline water in this order, then was dried on anhydrous sodium sulfate and the solvent distilled off under reduced pressure. The residue was purified by silica gel medium pressure column chromatography to obtain the above-referenced compound Octanoyl-Leu-Leu-CH2F (200 mg, 0.52 mmole) at a yield of 52%.

Workup

  1. customAfter the end of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe resultant residue was dissolved in anhydrous methylene chloride (5 ml)
  4. additionTo this, under ice water, were added triethylamine (0.23 g) and octanoylchloride (0.2 g)
  5. dissolutionto dissolve it
  6. washthis was washed with a 10% aqueous citric acid solution
  7. dry with materiala 5% sodium hydrogencarbonate, then a saturated saline water in this order, then was dried on anhydrous sodium sulfate
  8. distillationthe solvent distilled off under reduced pressure
  9. customThe residue was purified by silica gel medium pressure column chromatography

Sources & evidence

ORD record
ord-786c2955d74642719057ea4e411a5051
Source dataset
uspto-grants-1995_03
Patent number
US05399743

Reaction notes

Loading…