Benzoyl chloride → HCID 14694795, compound

HRID 2372876Notes

Reaction equation

HRID 2372876 reaction equation
[NH:1]([C:33](OC(C)(C)C)=[O:34])[CH2:2][C:3]([N:5]1[CH2:32][CH2:31][CH2:30][C@H:6]1[C:7]([NH:9][C@H:10]([C:15]([NH:17][CH2:18][C:19]([NH:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])=[O:4].C(Cl)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=O>>[NH:1]([C:33]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:34])[CH2:2][C:3]([N:5]1[CH2:32][CH2:31][CH2:30][C@H:6]1[C:7]([NH:9][C@H:10]([C:15]([NH:17][CH2:18][C:19]([NH:21][O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])=[O:4]

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 14694712HCID 14694712, compound

Product 1

HCID 14694795HCID 14694795, compoundYield 78%

Conditions

Temperature
-20 °C

Procedure

To Boc-Gly-Pro-Leu-Gly-NHOBzl (0.55 g; 1.00 mmol) obtained in Example 1 (F) was added under ice cooling 4.5N HCl/AcOEt (2 ml), and the mixture was brought back to room temperature. The reaction was carried out for 1 hour. The solvent was distilled off under reduced pressure and the residue was dissolved in DMF (5 ml). The solution was cooled with a coolant at -20° C. and TEA (0.14 ml; 1.00 mmol) was added dropwise. Bz-Cl (0.17 g; 1.21 mmol) was then added dropwise and TEA was used to adjust the pH to 8-9. The reaction was carried out for 1 hour and insolubles were filtered off. The solvent was distilled off under reduced pressure. The residue was dissolved in AcOEt, and the solution was washed successively with water, 1N-HCl, water, 10% Na2CO3 and water and then dried over anhydrous MgSO4. The solvent was distilled off under reduced pressure and the residue was purified by chromatography on silica gel (Fuji Davison BW 200, 25 g; eluted with CHCl3 :MeOH (=20:1) mixed solvent) to give Bz-Gly-Pro-Leu-Gly-NHOBzl (0.43 g; 78%) as a colorless powder. m.p. 79°-84° C.,specific rotation [α]D28 -69.0 (c=1.0, EtOH).

Workup

  1. additionwas added under ice cooling 4.5N HCl/AcOEt (2 ml)
  2. customwas brought back to room temperature
  3. distillationThe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in DMF (5 ml)
  5. waitThe reaction was carried out for 1 hour
  6. filtrationinsolubles were filtered off
  7. distillationThe solvent was distilled off under reduced pressure
  8. dissolutionThe residue was dissolved in AcOEt
  9. washthe solution was washed successively with water, 1N-HCl, water, 10% Na2CO3 and water
  10. dry with materialdried over anhydrous MgSO4
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe residue was purified by chromatography on silica gel (Fuji Davison BW 200, 25 g; eluted with CHCl3 :MeOH (=20:1) mixed solvent)

Sources & evidence

ORD record
ord-1f0711e5668249d4b7361d1cc54634ea
Source dataset
uspto-grants-1992_03
Patent number
US05100874

Reaction notes

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