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

HRID 216647

Reaktionsgleichung

Reaktionsgleichung von HRID 216647
C([O-])(O)=O.[Na+].Cl.[NH2:7][C@@H:8]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([OH:32])[CH:26]=1)[C:9]([O:11][CH2:12][C@H:13]([O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17])[CH3:14])=[O:10].[CH3:33][S:34]([OH:37])(=[O:36])=[O:35].CCOC(C)=O>O>[S:34]([OH:37])(=[O:36])(=[O:35])[CH3:33].[NH2:7][C@@H:8]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([OH:32])[CH:26]=1)[C:9]([O:11][CH2:12][C@H:13]([O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17])[CH3:14])=[O:10]

Komponenten

6

Edukt 4

HCID 6395Methanesulfonic Acid2×HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 11582017(2R)-2-Phenylcarbonyloxypropyl (2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoate Hydrochloride

Produkt 1

HCID 16125134(2R)-2-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylateAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of NaHCO3 (9.87 g, 117.5 mmol) in water (80 mL) was slowly added to a solution of the hydrochloride salt 3 (31.0 g, 78.3 mmol) in water (300 mL). The resulting aqueous suspension was extracted with EtOAc (2×400 mL). The combined EtOAc extract was washed with water, then brine, and dried through MgSO4. Methanesulfonic acid (6.04 mL, 93.12 mmol) was slowly added to the EtOAc solution while stirred. White precipitate formed as soon as the addition of methanesulfonic acid was complete. The suspension was stirred for another 30 min and then filtered. The filter cake was washed three times with EtOAc and vacuum dried overnight to afford 35.4 g (quantitative) of the mesylate salt 1 as a white solid. 1H NMR (400 MHz, CD3OD): δ 1.40 (d, J=6.4 Hz, 3H), 2.70 (s, 3H), 2.98 (dd, J=7.8, 14.6 Hz, 1H), 3.10 (dd, J=5.6, 14.4 Hz, 1H), 4.24 (dd, J=5.8, 7.8 Hz, 1H), 4.38 (dd, J=6.8, 12.0 Hz, 1H), 4.52 (dd, J=3.4, 11.8 Hz, 1H), 5.40 (dp, J=3.2, 6.4 Hz, 1H), 6.52 (dd, J=2.2, 8.2 Hz, 1H), 6.67 (d, J=2.2 Hz, 1H), 6.69 (d, J=8.0 Hz, 1H), 7.47 (t, J=7.6 Hz, 2H), 7.60 (br t, J=7.4 Hz, 1H), 8.01 (d, J=7.6 Hz, 2H). MS (ESI) m/z 360.07 (M+H)+ and 358.01 (M−H)−.

Aufarbeitung

  1. extractionThe resulting aqueous suspension was extracted with EtOAc (2×400 mL)
  2. extractionThe combined EtOAc extract
  3. washwas washed with water
  4. dry with materialbrine, and dried through MgSO4
  5. customWhite precipitate
  6. customformed as
  7. stirringThe suspension was stirred for another 30 min
  8. filtrationfiltered
  9. washThe filter cake was washed three times with EtOAc and vacuum
  10. customdried overnight

Quellen und Nachweise

ORD-Eintrag
ord-ac7c66999a9c49b1b394a52d677b6e44
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193242B2

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