Hydrochloric Acid → 5-Benzyloxycarbonylamino-8-guanidino-4-oxo-2-phenylmethyloctanoic acid

HRID 543153Notes

Reaction equation

HRID 543153 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([C:21]([OH:23])=[O:22])[CH2:9][C:10]([C@@H:12]([NH2:20])[CH2:13][CH2:14][CH2:15][N:16]=[C:17]([NH2:19])[NH2:18])=[O:11])=[CH:3][CH:2]=1.Cl.C(=O)([O-])O.[Na+].[CH2:30]([O:37][C:38](SC1N=C(C)C=C(C)N=1)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl>O1CCOCC1.O>[CH2:30]([O:37][C:38]([NH:20][CH:12]([CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH2:19])=[NH:18])[C:10](=[O:11])[CH2:9][CH:8]([CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:21]([OH:23])=[O:22])=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 563496Benzyl S-4,6-dimethylpyrimidin-2-yl thiocarbonateHCID 5487157Benzenepropanoic acid, alpha-[3-amino-6-[(aminoiminomethyl)amino]-2-oxohexyl]-, monohydrochloride, [S-(R*,S*)]-

Product 1

HCID 1785129595-Benzyloxycarbonylamino-8-guanidino-4-oxo-2-phenylmethyloctanoic acidYield 60.7%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Arphamenine A hydrochloride (150 mg), sodium hydrogen carbonate (176 mg) and S-benzyloxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (230 mg) were dissolved in 20 ml of dioxane-water (1:1), and the resultant solution was stirred at room temperature overnight. After the reaction was completed, the reaction solution was adjusted to pH 2.0 with 1N hydrochloric acid, followed by extraction with n-butanol. The extract in n-butanol was washed with water and concentrated to dryness. The residue obtained was chromatographed in a column of silica-gel (20 g) by eluting with a mixture of chloroform and methanol, while changing the ratio of chloroform to methanol in said mixture gradiently from 15:1 to 2:1. The desired reaction product was eluted out in fraction Nos. 60 to 120 [in chloroformmethanol (2:1)] of the eluate. These fractions were combined together and concentrated to dryness to afford 116 mg of the titled compound as a colorless powder. This product gave a value of m/z 455 (MH+) in mass spectrometry.

Workup

  1. extractionfollowed by extraction with n-butanol
  2. extractionThe extract in n-butanol
  3. washwas washed with water
  4. concentrationconcentrated to dryness
  5. customThe residue obtained
  6. customwas chromatographed in a column of silica-gel (20 g)
  7. washby eluting with a mixture of chloroform and methanol
  8. customThe desired reaction product
  9. washwas eluted out in fraction Nos
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9e82d5d4b10442d5803285e16c069a47
Source dataset
uspto-grants-1987_04
Patent number
US04661495

Reaction notes

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