Methanesulfonic Acid → (2R)-2-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate

HRID 216648

Reaction equation

HRID 216648 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].C(OC([NH:13][C@@H:14]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([OH:38])[CH:32]=1)[C:15]([O:17][CH2:18][C@H:19]([O:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23])[CH3:20])=[O:16])=O)(C)(C)C.C(OC)(C)(C)C>O1CCOCC1>[S:2]([OH:5])(=[O:4])(=[O:3])[CH3:1].[NH2:13][C@@H:14]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([OH:38])[CH:32]=1)[C:15]([O:17][CH2:18][C@H:19]([O:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23])[CH3:20])=[O:16]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 15413tert-Butyl methyl etherHCID 46899463(2R)-2-Phenylcarbonyloxypropyl(2S)-2-(tert-Butoxycarbonyl)amino-3-(3,4-dihydroxyphenyl)propanoate

Product 1

HCID 16125134(2R)-2-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylateYield 54.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methanesulfonic acid (3.9 mL, 60.1 mmol) was slowly added to a solution of (2R)-2-phenylcarbonyloxypropyl (2S)-2-(tert-butoxycarbonyl)amino-3-(3,4-dihydroxyphenyl)propanoate 2 (11.0 g, 22.1 mmol) in 1,4-dioxane (30 mL) while stirred at room temperature. The reaction mixture was stirred for 2 h. The solution was slowly added to methyl tert-butyl ether (MTBE) (600 mL) with vigorous stirring. The resulting suspension was filtered. The filter cake was washed three times with methyl tert-butyl ether and air dried to afford 5.48 g (54% yield) of the mesylate salt 1 as an off-white solid.

Workup

  1. stirringThe reaction mixture was stirred for 2 h
  2. filtrationThe resulting suspension was filtered
  3. washThe filter cake was washed three times with methyl tert-butyl ether and air
  4. customdried

Sources & evidence

ORD record
ord-9d4102aa4648481fb3d051f2e028eb85
Source dataset
uspto-grants-2012_06
Patent number
US08193242B2

Linked notes

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