Trifluoroacetic acid → 2-((S)-2-amino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester

HRID 2222950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2222950
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:28])[C@@H:12]([NH:20]C(OC(C)(C)C)=O)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:28])[C@@H:12]([NH2:20])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 866040392-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester

Produkt 1

HCID 866040402-((S)-2-amino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester (2.4 g, 5.919 mmol) was mixed in dichloromethane (25 mL) in an ice-bath. Trifluoroacetic acid (18 mL, 235 mmol) was added and the solution was stirred for 1.5 hours. The reaction mixture was evaporated and the residue was triturated with ether. The suspension was stirred vigorously for 10 minutes and then filtered. The solid was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with brine and dried over sodium sulfate. Evaporation of the solvents gave 2-((S)-2-amino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester as an off white solid (1.58 g, 87%).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customthe residue was triturated with ether
  3. stirringThe suspension was stirred vigorously for 10 minutes
  4. filtrationfiltered
  5. customThe solid was partitioned between aqueous sodium bicarbonate and dichloromethane
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with dichloromethane
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over sodium sulfate
  10. customEvaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-11eca7577ba64c9485a0dfc3f4f9b84c
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07371869B2

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