Monoperoxyphthalic Acid Magnesium Salt → HCID 86613450, compound

HRID 507827Notes

Reaction equation

HRID 507827 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=1[C:9]([NH:11][CH2:12][C@H:13]([CH:26]([CH3:28])[CH3:27])[CH2:14][C@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:16]=[CH2:17])=[O:10].C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:37].[Mg+2]>CO>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=1[C:9]([NH:11][CH2:12][C@H:13]([CH:26]([CH3:27])[CH3:28])[CH2:14][C@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])[C@@H:16]1[CH2:17][O:37]1)=[O:10]

Participants

4

Reactant 2

HCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 86613451tert-Butyl (3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methyl-1(S)-vinylpentyl)carbamate

Product 1

HCID 86613450HCID 86613450, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 1.48 g of tert-butyl (3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methyl-1(S)-vinylpentyl)carbamate in 30 ml of methanol is admixed with 7.81 g of magnesium monoperoxyphthalate and stirred over 72 hours. The reaction mixture is poured onto water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a yellowish oil. Rf=0.30 (1:1 EtOAc-heptane, run 2×); Rt=18.64 (gradient II).

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionextracted with tert-butyl methyl ether (2×)
  3. washThe combined organic phases are washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1ed91074025e403d8d8a96b4629661c0
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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