Triethylamine → 3-Methanesulfonyloxy-1-[4-(thiophene-2-carbonyl-amino)methyl-1,3-thiazol-2-yl]azetidine

HRID 891785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891785
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[S:7][CH:8]=[C:9]([CH2:11][NH:12][C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)=[O:14])[N:10]=2)[CH2:3]1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>C(Cl)Cl>[CH3:20][S:21]([O:1][CH:2]1[CH2:5][N:4]([C:6]2[S:7][CH:8]=[C:9]([CH2:11][NH:12][C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)=[O:14])[N:10]=2)[CH2:3]1)(=[O:23])=[O:22]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 222428533-Hydroxy-1-[4-(thiophene-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidine

Produkt 1

HCID 222427473-Methanesulfonyloxy-1-[4-(thiophene-2-carbonyl-amino)methyl-1,3-thiazol-2-yl]azetidineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-hydroxy-1-[4-(thiophene-2-carbonyl-amino)methyl-1,3-thiazol-2-yl]azetidine (571 mg, 1.93 mmol) (obtained as described in Reference Example 66(2)) in methylene chloride (28 ml) were added methanesulfonyl chloride (0.18 ml, 2.32 mmol) and triethylamine (0.33 ml, 2.32 mmol) in an ice bath and the mixture was stirred for 1 hour. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (1:1) as the eluant to afford 3-methanesulfonyloxy-1-[4-(thiophene-2-carbonyl-amino)methyl-1,3-thiazol-2-yl]azetidine (490 mg, yield 91%) as a pale yellow solid.

Aufarbeitung

  1. customthe completion of the reaction
  2. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-02901b7fc00c478da3c2b27618b46563
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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