Water → HCID 66868851, Verbindung

HRID 1949725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1949725
[Si:1]([O:8][CH2:9][CH2:10][N:11]([C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][C:30]=1[Cl:39])[C:12]([C:14]1[S:28][C:17]2[C:18]3[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:19]=3[O:20][CH2:21][CH2:22][C:16]=2[CH:15]=1)=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O1CCCC1.O.O.[OH-].[Li+]>>[Si:1]([O:8][CH2:9][CH2:10][N:11]([C:29]1[CH:38]=[CH:37][C:32]([C:33]([OH:35])=[O:34])=[CH:31][C:30]=1[Cl:39])[C:12]([C:14]1[S:28][C:17]2[C:18]3[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:19]=3[O:20][CH2:21][CH2:22][C:16]=2[CH:15]=1)=[O:13])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Komponenten

5

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66868514methyl 4-(N-(2-(tert-butyldimethylsilyloxy)ethyl)-10-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-3-chlorobenzoate

Produkt 1

HCID 66868851HCID 66868851, VerbindungAusbeute 60 %

Versuchsvorschrift

To a solution of methyl 4-(N-(2-(tert-butyldimethylsilyloxy)ethyl)-10-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-3-chlorobenzoate (0.250 g, 0.436 mmol) in tetrahydrofuran (10.2 mL, 126 mmol) and water (10.2 mL, 566 mmol) was added lithium hydroxide, monohydrate (0.0732 g, 1.74 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated, acidified with 1M HCl, and extracted with DCM (3×). The combined organics were dried (Na2SO4), filtered and concentrated to give 4-(N-(2-(tert-butyldimethylsilyloxy)ethyl)-10-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-3-chlorobenzoic acid (yield 60%). MS: (ESI+) 559.1

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with DCM (3×)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7f0f2a2dd68949458173a7df42c4ef0d
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399690B2

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