Acetic Acid → N-(2-chlorophenyl)-N-(2-hydroxyethyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

HRID 84414

Reaktionsgleichung

Reaktionsgleichung von HRID 84414
[Si]([O:8][CH2:9][CH2:10][N:11]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:34])[C:12]([C:14]1[S:27][C:17]2[C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[O:20][CH2:21][CH2:22][C:16]=2[CH:15]=1)=[O:13])(C(C)(C)C)(C)C.C(O)(=O)C.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[N:11]([CH2:10][CH2:9][OH:8])[C:12]([C:14]1[S:27][C:17]2[C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[O:20][CH2:21][CH2:22][C:16]=2[CH:15]=1)=[O:13]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 57900150N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Produkt 1

HCID 44242097N-(2-chlorophenyl)-N-(2-hydroxyethyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamideAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide (0.030 g, 0.058 mmol) in acetic acid (0.0033 mL, 0.058 mmol) and tetrahydrofuran (0.3 mL, 4 mmol) was added 1 M of tetrabutylammonium fluoride hydrate in tetrahydrofuran (0.058 mL). The reaction was stirred at room temperature w/TLC and LC/MS monitor. Deprotection was complete after overnight stirring. The reaction mixture was concentrated in vacuo, taken into ethylacetate and washed with water/saline and concentrated to a glassy residue, which was purified by MPLC, eluting with ethylacetate/hexanes, gradient 0-50% B to give 22.4 mg of 106 (yield 40%). MS: (ESI+) 401

Aufarbeitung

  1. stirringstirring
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. washwashed with water/saline
  4. concentrationconcentrated to a glassy residue, which
  5. customwas purified by MPLC
  6. washeluting with ethylacetate/hexanes, gradient 0-50% B

Quellen und Nachweise

ORD-Eintrag
ord-a8577833b1ff4d7ca60f7e095452f467
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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