Sulfuric Acid → methyl (S)-3-(4-hydroxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoate

HRID 517505Notes

Reaction equation

HRID 517505 reaction equation
S(=O)(=O)(O)O.[CH3:6][S:7]([N:10]1[CH2:15][CH2:14][N:13]([C@@H:16]([CH2:21][NH:22][C:23](=[O:37])[C:24]2[CH:29]=[CH:28][C:27]([O:30]COCCOC)=[CH:26][CH:25]=2)[C:17]([O:19][CH3:20])=[O:18])[CH2:12][CH2:11]1)(=[O:9])=[O:8].C(=O)([O-])O.[Na+]>O1CCCC1.CO>[OH:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]([NH:22][CH2:21][C@H:16]([N:13]2[CH2:12][CH2:11][N:10]([S:7]([CH3:6])(=[O:9])=[O:8])[CH2:15][CH2:14]2)[C:17]([O:19][CH3:20])=[O:18])=[O:37])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 67056964methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-[4-(2-methoxyethoxymethoxy)benzoyl-amino]propanoate

Product 1

HCID 67056914methyl (S)-3-(4-hydroxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoateYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.5 ml of 98% sulphuric acid are added to a solution of 1.6 g (3.4 mmol) of methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-[4-(2-methoxyethoxymethoxy)benzoyl-amino]propanoate in 15 ml of tetrahydrofuran and 15 ml of methanol. After stirring for 18 h at ambient temperature, the reaction medium is hydrolysed with a saturated aqueous solution of sodium hydrogen carbonate then extracted with ethyl acetate. The organic phase is washed with water then with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated. 1.1 g (85%) of methyl (S)-3-(4-hydroxybenzoylamino)-2-(4-methane-sulphonylpiperazin-1-yl)propanoate are obtained in the form of a white solid.

Workup

  1. extractionthen extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d933a0cc94694dee97f6ea46920f8f16
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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