Hydrochloric Acid → HCID 178445922, compound

HRID 464898Notes

Reaction equation

HRID 464898 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([NH:22][C@H:23]([C:30]([NH:32]N)=[O:31])[CH2:24][C:25]1[N:29]=[CH:28][NH:27][CH:26]=1)=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N(OCCC(C)C)=O.CN1CCOCC1.N[C@H:51]([CH2:56][OH:57])[CH2:52][CH:53]([CH3:55])[CH3:54]>O1CCOCC1.CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([NH:22][C@H:23]([C:30]([NH:32][C@H:51]([CH2:56][OH:57])[CH2:52][CH:53]([CH3:55])[CH3:54])=[O:31])[CH2:24][C:25]1[N:29]=[CH:28][NH:27][CH:26]=1)=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 8053Isoamyl NitriteHCID 111307L-LeucinolHCID 178514451HCID 178514451, compound

Product 1

HCID 178445922HCID 178445922, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of 0.91 g. (2 mmole) of N-benzyloxycarbonyl-L-phenylalanyl-L-histidine hydrazide in 32 ml. of dimethylformamide was added 1.64 ml. of a 4.1N solution of hydrogen chloride in dioxane. The mixture was cooled to -60° C., and there was added 0.4 ml. of isopentyl nitrite. The temperature of the resulting mixture was then raised to -20° C. After confirming the disappearance of the hydrazide, the temperature of the mixture was lowered to -60° C., and then the mixture was neutralized by the addition of 0.8 g. of N-methylmorpholine. To the mixture was added 0.28 g. (2.4 mmole) of L-leucinol and the mixture was stirred at 4° C. for 23 hours; the solvent was then removed by distillation under reduced pressure, and water was added to the residue to form a colourless precipitate, which was separated by filtration and washed thoroughly with water and then with ethyl acetate. There was obtained 0.94 g. of the desired compound as a white powdery solid, melting at 181°-183° C.; [α]22 -19.4° (C=0.5, methanol).

Workup

  1. additionthere was added 0.4 ml
  2. temperatureThe temperature of the resulting mixture was then raised to -20° C
  3. customwas lowered to -60° C.
  4. additionthe mixture was neutralized by the addition of 0.8 g
  5. additionTo the mixture was added 0.28 g
  6. customthe solvent was then removed by distillation under reduced pressure, and water
  7. additionwas added to the residue
  8. customto form a colourless precipitate, which
  9. customwas separated by filtration
  10. washwashed thoroughly with water
  11. customThere was obtained 0.94 g

Sources & evidence

ORD record
ord-4f310c592fc8481e843908b8c8f49261
Source dataset
uspto-grants-1985_10
Patent number
US04548926

Reaction notes

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