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Trifluoroacetic acid → N-[(4aR,7aR)-7a-Isothiazol-5-yl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

HRID 1619036
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1619036
[C:1]([NH:9][C:10]1[S:11][CH2:12][C@@H:13]2[CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][C@:14]2([C:26]2[S:30][N:29]=[CH:28][CH:27]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C[C@@H]2[C@@](C3SC=C(Br)C=3)(N=C(NC(=O)C3C=CC=CC=3)SC2)C1)C=C.FC(F)(F)C(O)=O>ClCCl>[S:30]1[C:26]([C@:14]23[CH2:16][NH:17][CH2:18][C@H:13]2[CH2:12][S:11][C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:15]3)=[CH:27][CH:28]=[N:29]1
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Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 86762226tert-butyl (4aR,7aR)-2-benzamido-7a-isothiazol-5-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylateHCID 86762227N-[(4aR,7aR)-6-Allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Produkt 1

HCID 86762225N-[(4aR,7aR)-7a-Isothiazol-5-yl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a room temperature solution of tert-butyl (4aR,7aR)-2-benzamido-7a-isothiazol-5-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate, isomer 2 (1.26 g, 2.83 mmol) in dichloromethane (25 mL) is added trifluoroacetic acid (4.29 mL, 56.68 mmol) drop wise. The resultant solution is stirred for 18 hours at ambient temperature. The solvent is removed under vacuum. The mixture is diluted with ethyl acetate followed by saturated sodium bicarbonate. The layers are separated and the aqueous phase is re-extracted with ethyl acetate (3×). The combined organic layers are dried over sodium sulfate and the solvent is removed under vacuum to give the title compound (850 mg, 2.46 mmol, 87%). ES/MS (m/e): 345 (M+H).

Aufarbeitung

  1. customThe solvent is removed under vacuum
  2. additionThe mixture is diluted with ethyl acetate
  3. customThe layers are separated
  4. extractionthe aqueous phase is re-extracted with ethyl acetate (3×)
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. customthe solvent is removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b81dc801ecd64bc08f503f317f4cf3e4
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08772282B2

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