Water → HCID 66868851, Verbindung

HRID 2078830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2078830
[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-500253bb9c2c4c46a5e969e5e2f3430b
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928248B2

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