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Sodium Hydroxide → 4-((2S,4S)-1-(7-Fluoro-2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-fluoro-2-pyrrolidinylmethoxy)benzoic acid

HRID 1372576
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1372576
[F:1][C:2]1[C:10]2[O:9][C:8]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:19][C:20]([N:22]1[CH2:26][C@@H:25]([F:27])[CH2:24][C@H:23]1[CH2:28][O:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36]C)=[O:35])=[CH:32][CH:31]=1)=[O:21].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[C:10]2[O:9][C:8]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:19][C:20]([N:22]1[CH2:26][C@@H:25]([F:27])[CH2:24][C@H:23]1[CH2:28][O:29][C:30]1[CH:31]=[CH:32][C:33]([C:34]([OH:36])=[O:35])=[CH:38][CH:39]=1)=[O:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 58778812Methyl 4-((2S,4S)-1-(7-fluoro-2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-fluoro-2-pyrrolidinylmethoxy)benzoate

Produkt 1

HCID 587786284-((2S,4S)-1-(7-Fluoro-2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-fluoro-2-pyrrolidinylmethoxy)benzoic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 4-((2S,4S)-1-(7-fluoro-2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-fluoro-2-pyrrolidinylmethoxy)benzoate (490 mg, 0.915 mmol) was dissolved in THF (40 ml). To the resulting solution was added 0.25N NaOH (40 ml), followed by stirring at room temperature for 14 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue was acidified with 1N HCl, followed by extraction with a chloroform/methanol (10/1) mixture. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from chloroform/methanol (20/1) eluate fractions, the title compound (394 mg, 83%) was obtained as a colorless amorphous substance.

Aufarbeitung

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. extractionfollowed by extraction with a chloroform/methanol (10/1) mixture
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from chloroform/methanol (20/1) eluate fractions

Quellen und Nachweise

ORD-Eintrag
ord-f8b7663c60644894864453c0656c7adc
Quelldatensatz
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07157487B2

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