Sulfuric acid magnesium salt (1:1) → HCID 59204396, compound

HRID 2241875Notes

Reaction equation

HRID 2241875 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[CH:10]([CH2:13][CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[OH:16])[CH:9]2[C:24]2[CH:33]=[CH:32][C:27]([C:28]([NH:30]O)=[NH:29])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.[H][H].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.N.[Ni]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:11](=[O:12])[CH:10]([CH2:13][CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[OH:16])[CH:9]2[C:24]2[CH:33]=[CH:32][C:27]([C:28]([NH2:30])=[NH:29])=[CH:26][CH:25]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 178418361HCID 178418361, compoundHCID 178513265HCID 178513265, compound

Product 1

HCID 59204396HCID 59204396, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 8028TetrahydrofuranSolvent

Procedure

100 mg of 4-{1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}-N-hydroxybenzamidine (3) were dissolved in 100 ml of tetrahydrofuran and, with 2 ml of conc. ammonia, hydrogenated over Raney nickel at a hydrogen pressure of 75 bar and 25° C. for 30 hours. After addition of magnesium sulfate, the reaction solution was filtered. The filtrate was concentrated and separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoro-acetic acid)=80/20→10/90). This gave the product of molecular weight 435.48 (C25H23F2N3O2); MS (ESI): 436.18 (M+H+).

Workup

  1. filtrationthe reaction solution was filtered
  2. concentrationThe filtrate was concentrated
  3. customseparated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoro-acetic acid)=80/20→10/90)
  4. customThis gave the product of molecular weight 435.48 (C25H23F2N3O2)

Sources & evidence

ORD record
ord-a68b0eaf62e34802b89f76cfd94ff9e4
Source dataset
uspto-grants-2010_03
Patent number
US07671047B2

Reaction notes

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