Protocatechuic Acid → HCID 22855045, compound

HRID 1755838Notes

Reaction equation

HRID 1755838 reaction equation
[NH2:1][C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6]([CH2:14][S:15][C:16]1[N:21]3[N:22]=[C:23]([CH2:25][OH:26])[N:24]=[C:20]3[N:19]=[C:18]([CH3:27])[CH:17]=1)=[C:7]2[C:11]([OH:13])=[O:12].[OH:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[OH:38])[C:32](O)=[O:33].B(F)(F)F>C(#N)C>[NH2:1][C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6]([CH2:14][S:15][C:16]1[N:21]3[N:22]=[C:23]([CH2:25][O:26][C:32](=[O:33])[C:31]4[CH:35]=[CH:36][C:37]([OH:38])=[C:29]([OH:28])[CH:30]=4)[N:24]=[C:20]3[N:19]=[C:18]([CH3:27])[CH:17]=1)=[C:7]2[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 72Protocatechuic AcidHCID 6356Boron trifluoride2×HCID 15672736HCID 15672736, compound

Product 1

HCID 22855045HCID 22855045, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

(6R,7R)-7-Amino-3-[[[2-(hydroxymethyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (4.08 g) (known from EPOS 302,633) and 1.54 g of 3,4-dihydroxybenzoic acid are treated with 30 ml of a 20% solution of boron trifluoride in acetonitrile and stirred at room temperature for 2 hours. A further 25 ml of a 20% solution of boron trifluoride in acetonitrile are added; the reaction mixture is stirred at room temperature under argon for 2 days. After the addition of 100 ml of ice-water the reaction mixture is concentrated to about half. The product is precipitated by adjusting the pH value to 2.0 with concentrated aqueous ammonia. The precipitated material is suspended in water, brought into solution with 1N aqueous sodium hydroxide solution and purified by chromatography on RP12-Kieselgel with water/acetonitrile. The product fractions are concentrated to about 50 ml and the product is precipitated by acidification to pH 2.0. After drying in a high vacuum there are obtained 1.60 g of (6R,7R)-7-amino-3-[[[2-[[(3,4-dihydroxybenzoyl)oxy]methyl]-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a white powder.

Workup

  1. stirringthe reaction mixture is stirred at room temperature under argon for 2 days
  2. concentrationis concentrated to about half
  3. customThe product is precipitated
  4. custompurified by chromatography on RP12-Kieselgel with water/acetonitrile
  5. concentrationThe product fractions are concentrated to about 50 ml
  6. customthe product is precipitated by acidification to pH 2.0
  7. customAfter drying in a high vacuum

Sources & evidence

ORD record
ord-2cb0d5531a6b4944916fc451acc30530
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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