Hydrochloric Acid → HCID 178525815, compound

HRID 1982326Notes

Reaction equation

HRID 1982326 reaction equation
O.[OH-].[Na+].[N:4]1([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH2:33][CH2:32][CH2:31][C@H:5]1[C:6]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:27]([O:29]C)=[O:28])[CH2:21][C:22]1[N:26]=[CH:25][NH:24][CH:23]=1)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7].Cl>CO>[N:4]1([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH2:33][CH2:32][CH2:31][C@H:5]1[C:6]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:27]([OH:29])=[O:28])[CH2:21][C:22]1[N:26]=[CH:25][NH:24][CH:23]=1)=[O:18])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178501417HCID 178501417, compound

Product 1

HCID 178525815HCID 178525815, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

35 ml of water and 5.0 ml of 1N sodium hydroxide solution are added to 1.92 g of Z-Pro-Phe-His-OMe (H. Derwald et al., J. Med. Chem. 7, 50 [1964]) dissolved in 50 ml of methanol. The solution is stirred for 45 minutes at 25° and then neutralised with 5.0 ml of 1N hydrochloric acid. The solvent is removed and the residue is flash-chromatographed over 10 g of silica gel (eluant: chloroform/methanol/concentrated aqueous ammonia solution [5:3:1]; fractions of approximately 15 ml). Fractions 6-13 are combined, concentrated by evaporation and the residue is dissolved in 70 ml of water. After neutralisation to a pH value of 5.0 by the addition of dilute hydrochloric acid, extraction is carried out twice with n-butanol and the combined butanol phases are washed with water and concentrated by evaporation. After drying the residue in a high vacuum, Z-Pro-Phe-His-OH is obtained in the form of a colourless powder; Rf (I)=0.23.

Workup

  1. customThe solvent is removed
  2. customthe residue is flash-chromatographed over 10 g of silica gel (eluant: chloroform/methanol/concentrated aqueous ammonia solution [5:3:1]; fractions of approximately 15 ml)
  3. concentrationconcentrated by evaporation
  4. dissolutionthe residue is dissolved in 70 ml of water
  5. additionAfter neutralisation to a pH value of 5.0 by the addition of dilute hydrochloric acid, extraction
  6. washthe combined butanol phases are washed with water
  7. concentrationconcentrated by evaporation
  8. customAfter drying the residue in a high vacuum

Sources & evidence

ORD record
ord-021d0b48e6f74cfdb3e57bd071aada36
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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