Hydrochloric Acid → HCID 178490240, compound

HRID 1419724Notes

Reaction equation

HRID 1419724 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C@@H:5]1[N:10]([C:11](=[O:33])[C@@H:12]([NH:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:9][CH2:8][N:7]([CH2:34][C:35]([OH:37])=[O:36])[C:6]1=[O:38].C([O-])(O)=O.[Na+].[ClH:44].O=C1N([O:55][C:56](=O)[C:57]2[CH:62]=[CH:61][C:60]([NH:63][C:64]([NH2:66])=[NH:65])=[CH:59][CH:58]=2)C(=O)C2C1C1CC2C=C1.Cl>O1CCOCC1>[ClH:44].[CH2:26]([O:25][C:23]([NH:22][C@@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:11]([N:10]1[CH2:9][CH2:8][N:7]([CH2:34][C:35]([OH:37])=[O:36])[C:6](=[O:38])[C@@H:5]1[CH2:4][CH2:3][CH2:2][NH:1][C:56](=[O:55])[C:57]1[CH:58]=[CH:59][C:60]([NH:63][C:64]([NH2:66])=[NH:65])=[CH:61][CH:62]=1)=[O:33])=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 54085635HCID 54085635, compoundHCID 178479385HCID 178479385, compound

Product 1

HCID 178490240HCID 178490240, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 50 ml of a 50% aqueous solution of dioxane was dissolved 0.5 g of (S,S)-3-(3-aminopropyl)-4-[2-benzyloxycarbonylamino-3-(4-methoxyphenyl)propionyl1-2-oxopiperazine-1-acetic acid produced in Reference Example 35. To the solution was added 0.24 g of NaHCO3, to which was then added 0.377 g of 4-guanidinobenzoic acid 3,5-dioxo-4-azatricyclo[5,2,1,0 2,6)deca-8-en-4-yl ester hydrochloride. The mixture was stirred for two hours at room temperature. The pH of the reaction mixture was adjusted to 3 with 1N-HCl, followed by distilling off dioxane. The residue was purified by means of a column chromatography (eluting with H2O→10% aqueous solution of CH3CN→a 20% aqueous solution of CH3CN→a 50% aqueous solution of CH3CN) to afford 0.43 g of the title compound.

Workup

  1. customproduced in Reference Example 35
  2. distillationby distilling off dioxane
  3. customThe residue was purified by means of a column chromatography (
  4. washeluting with H2O→10% aqueous solution of CH3CN→a 20% aqueous solution of CH3CN→a 50% aqueous solution of CH3CN)

Sources & evidence

ORD record
ord-a1cb95a92a5c4b9da9de5750554c3af5
Source dataset
uspto-grants-1999_03
Patent number
US05888531

Reaction notes

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