Lithium hydroxide, monohydrate → 7-[(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylic acid

HRID 132881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132881
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[F:40])[CH2:10][C:11]([N:13]1[CH2:22][C:21]2[N:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]([C:27]([O:29]CC)=[O:28])=[CH:17][C:16]=2[CH2:15][CH2:14]1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>O1CCCC1.CO.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[F:40])[CH2:10][C:11]([N:13]1[CH2:22][C:21]2[N:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]([C:27]([OH:29])=[O:28])=[CH:17][C:16]=2[CH2:15][CH2:14]1)=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 69222346Ethyl 7-[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylate

Produkt 1

HCID 692244927-[(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

A solution of the product from Step A above (92 mg, 0.161 mmol) in 1.2 mL of 3:2:1 tetrahydrofuran/methanol/water was treated with lithium hydroxide monohydrate (10 mg) and the solution was stirred at room temperature for 18 h. The volatiles were removed under a stream of nitrogen, and the residue was dissolved in 4 mL of water. The solution was acidified by portionwise addition of citric acid monohydrate, and the product was extracted into ethyl acetate. The combined organic extracts were dried over magnesium sulfate and concentrated to afford the title compound as a white foam.

Aufarbeitung

  1. customThe volatiles were removed under a stream of nitrogen
  2. dissolutionthe residue was dissolved in 4 mL of water
  3. additionThe solution was acidified by portionwise addition of citric acid monohydrate
  4. extractionthe product was extracted into ethyl acetate
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3b98789a5fe54851a756c4cb22efb505
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388019B2

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