Methanol → 7-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylic acid

HRID 1021360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1021360
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:33]=[CH:32][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:26]([O:28]C)=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[C:30]#[N:31])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].O.CO>C1COCC1.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:26]([OH:28])=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[C:30]#[N:31])=[CH:32][CH:33]=2)=[O:10])=[CH:34][CH:35]=1

Komponenten

8

Edukt 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 67080264Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylate

Produkt 1

HCID 670803677-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylic acidAusbeute 21,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (100 mg, 0.204 mmol) was diluted with THF (1 mL) followed by the addition of NaOH (0.204 mL, 1.02 mmol) and 500 μL of water and methanol. After stirring for 3 hours, the reaction was diluted with ethyl acetate and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified using the Horizon with a 25 cartridge and running a gradient 0.5% methanol/0.5% acetic acid/CH2Cl2 to 10% methanol/0.5% acetic acid/CH2Cl2 to yield the title compound (21 mg, 21.6% yield) as a white solid. MS (ESI)=476.9 (M+1).

Aufarbeitung

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe material was purified

Quellen und Nachweise

ORD-Eintrag
ord-4cdd9bd9c3de4145b38f8679e24330c0
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716498B2

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