Trifluoroacetic acid → HCID 178445918, compound

HRID 464906Notes

Reaction equation

HRID 464906 reaction equation
C(OC([NH:11][C@@H:12]([C:24]([OH:26])=O)[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.[N+](C1C=C([N+]([O-])=O)C=CC=1[NH:39][C@H:40]([C:47]([NH:49][C@H:50]([CH2:55][OH:56])[CH2:51][CH:52]([CH3:54])[CH3:53])=[O:48])[CH2:41][C:42]1[N:46]=[CH:45][NH:44][CH:43]=1)([O-])=O.FC(F)(F)[C:59]([OH:61])=[O:60].[C:64]1(OC)[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.[CH3:72]N1CCOCC1>>[CH2:72]([O:61][C:59]([NH:11][C@@H:12]([C:24]([NH:39][C@H:40]([C:47]([NH:49][C@H:50]([CH2:55][OH:56])[CH2:51][CH:52]([CH3:53])[CH3:54])=[O:48])[CH2:41][C:42]1[N:46]=[CH:45][NH:44][CH:43]=1)=[O:26])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:60])[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 79724-MethylmorpholineHCID 7020847HCID 7020847, compoundHCID 178445913HCID 178445913, compound

Product 1

HCID 178445918HCID 178445918, compound

Conditions

Temperature
0 °C

Procedure

A mixed acid anhydride was prepared in a conventional manner from 186 mg. (0.53 mmole) of N-benzyloxycarbonyl-3-(1-naphthyl)-D-alanine. Separately, 360 mg. (0.7 mmole) of N-t-butyroxycarbonyl-Nim -2,4-dinitrophenyl-L-histidyl-L-leucinol was treated with 6 ml. of trifluoroacetic acid in the presence of 80 mg. (0.7 mmole) of anisole at room temperature for 30 minutes. To the resulting mixture were added 100 ml. of diethyl ether, and the yellow powder thus precipitated was separated by filtration and dissolved in 5 ml. of dimethylformamide. The solution was cooled to 0° C. and neutralized with 70 mg. (0.7 mmole) of N-methyl-morpholine; to the mixture was added the above-prepared mixed acid anhydride. The mixture was stirred at 0° C. for 1 hour, allowed to stand overnight at room temperature and then concentrated by evaporation under reduced pressure. To the residue was added dilute hydrochloric acid, and the yellow oily substance formed was extracted with ethyl acetate. The organic layer was washed successively with water, a 5% w/v aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulphate. The solvent was removed by distillation under reduced pressure, and water was added to the residue to solidify it. The solidified mass was pulverized and separated by filtration, to afford 330 mg. of the title compound, which was used for the next reaction without purification.

Workup

  1. additionTo the resulting mixture were added 100 ml
  2. customof diethyl ether, and the yellow powder thus precipitated
  3. customwas separated by filtration
  4. dissolutiondissolved in 5 ml
  5. waitto stand overnight at room temperature
  6. concentrationconcentrated by evaporation under reduced pressure
  7. additionTo the residue was added dilute hydrochloric acid
  8. customthe yellow oily substance formed
  9. extractionwas extracted with ethyl acetate
  10. washThe organic layer was washed successively with water
  11. dry with materiala 5% w/v aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulphate
  12. customThe solvent was removed by distillation under reduced pressure, and water
  13. additionwas added to the residue
  14. customseparated by filtration
  15. customto afford 330 mg

Sources & evidence

ORD record
ord-c1f01919ab4447c28f2b0084f4f3b298
Source dataset
uspto-grants-1985_10
Patent number
US04548926

Reaction notes

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