Hydrogen Bromide → HCID 131718933, compound

HRID 1609363Notes

Reaction equation

HRID 1609363 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][CH2:12][CH2:13][CH3:14])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Br>C(O)(=O)C>[NH:1]([C:19]([CH2:17][CH2:15][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:21])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([CH2:17][F:18])=[O:16])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:8])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 131718934HCID 131718934, compound

Product 1

HCID 131718933HCID 131718933, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The Z-Leu-Nle-CH2F (0.29 g) obtained in Example 1 was dissolved in acetic acid (4.5 ml) including 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 cooling, were added triethylamine (0.20 g) and octanoylchloride (0.12 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 a reduced pressure. The residue was purified by silica gel medium pressure column chromatography to obtain the above-referenced compound Octanoyl-Leu-Nle-CH2F (120 mg, 0.31 mmole) at a yield of 42%.

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 cooling, were added triethylamine (0.20 g) and octanoylchloride (0.12 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 a reduced pressure
  9. customThe residue was purified by silica gel medium pressure column chromatography

Sources & evidence

ORD record
ord-5b2f53315913414a8705c8fccf9b9220
Source dataset
uspto-grants-1995_03
Patent number
US05399743

Reaction notes

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