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Methanol → (+/-)-C,C,C-Trifluoro-N-{3-[6-(5-fluorobenzothiazol-2-ylmethoxy)-trans-2-methyl-4-oxochroman-3-ylmethyl]phenyl}methanesulfonamide

HRID 1684633
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1684633
[F:1][C:2]([F:39])([F:38])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:26][C:27]4[S:28][C:29]5[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:30]=5[N:31]=4)[CH:21]=3)[O:16][C:15]=2[CH3:37])[CH:8]=1)(=[O:5])=[O:4].CO>O1CCCC1.ClCCl>[F:39][C:2]([F:1])([F:38])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C@@H:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:26][C:27]4[S:28][C:29]5[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:30]=5[N:31]=4)[CH:21]=3)[O:16][C@H:15]2[CH3:37])[CH:8]=1)(=[O:5])=[O:4]
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Komponenten

5

Edukt 2

HCID 887MethanolHCID 19039946C,C,C-Trifluoro-N-{3-[6-(5-fluorobenzothiazol-2-ylmethoxy)-2-methyl-4-oxo-4H-chromen-3-ylmethyl]phenyl}methanesulfonamide

Produkt 1

HCID 131720055(+/-)-C,C,C-Trifluoro-N-{3-[6-(5-fluorobenzothiazol-2-ylmethoxy)-trans-2-methyl-4-oxochroman-3-ylmethyl]phenyl}methanesulfonamideAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344Dichloromethane
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred suspension of 2.59 g (4.48 mmole) product from Example 127 in 100 mL tetrahydrofuran was added dropwise 9 mL (9.40 mmole) UB(sec-butyl)3H (1M in THF, L-Selectride®) at -78° C. The mixture was stirred for 2 hours, then quenched with 5% ammonium chloride. The mixture was poured into water, acidified to ph 1-4 with 1N HCl, and extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine and dried (MgSO4) and concentrated to give an oil. Flash chromatography on silica gel eluting with 2.5% methanol in dichloromethane afforded 1.4 g (54%) of the title product as a solid, mp 183°-185° C. Analysis calculated for C26H20N2S2O5F4 : C, 53.79; H, 3.47; N, 4.83. Found: C, 53.25; H, 3.23; N, 4.45.

Aufarbeitung

  1. additionwas added dropwise 9 mL (9.40 mmole) UB(sec-butyl)3H (1M in THF, L-Selectride®) at -78° C
  2. customquenched with 5% ammonium chloride
  3. additionThe mixture was poured into water
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-487f3965e776490b9ce9570a88f28f26
Quelldatensatz
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05641789

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