Hydrochloric Acid → HCID 86754002, compound

HRID 1419848Notes

Reaction equation

HRID 1419848 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[C:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].Cl>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:20][CH:19]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 54063198HCID 54063198, compound

Product 1

HCID 86754002HCID 86754002, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of the product (4 g) obtained in example 1 in methanol (40 ml) at room temperature, magnesium turnings (3.8 g) were added and the reaction mixture was stirred at the same temperature for 1 h. The reaction mixture was added to ice water (20 ml), the pH was adjusted to 6.5-7.0 using 10% aqueous hydrochloric acid and the solution was extracted with chloroform (3×100 ml). The combined organic extract was washed with H2O, dried (CaCl2) and the solvent was removed under reduced pressure. The residual mass was chromatographed on silica gel using 0.4% methanol in chloroform to give 2.4 g (68%) of the title compound. mp 72°-74° C.

Workup

  1. extractionthe solution was extracted with chloroform (3×100 ml)
  2. extractionThe combined organic extract
  3. washwas washed with H2O
  4. dry with materialdried (CaCl2)
  5. customthe solvent was removed under reduced pressure
  6. customThe residual mass was chromatographed on silica gel using 0.4% methanol in chloroform

Sources & evidence

ORD record
ord-6018d3d5ec344643843aa4c39a0a9ffe
Source dataset
uspto-grants-1999_03
Patent number
US05889025

Reaction notes

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