Acetic Acid → HCID 22730010, Verbindung

HRID 2085786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085786
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=2)=[C:5]([O:19][CH3:20])[CH:4]=1)=O.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C([BH3-])#N.[Na+].C(O)(=O)C>C1COCC1.CO.C(OCC)(=O)C>[CH3:20][O:19][C:5]1[CH:4]=[C:3]([CH2:1][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:8]=[CH:7][C:6]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 11558086Methyl 4'-formyl-2'-methoxy[1,1'-biphenyl]-4-carboxylate

Produkt 1

HCID 22730010HCID 22730010, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of Example 122I (135 mg, 0.50 mmol), morpholine (100 mg), 1M sodium cyanoborohydride in THF (1 mL) in methanol (2 mL) and acetic acid (0.3 mL) was stirred for 18 hours, diluted with ethyl acetate (100 mL), washed sequentially with 2M sodium carbonate (10 mL), water (20 mL), and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30-100% ethyl acetate/hexanes to provide the desired product. MS (DCI(+)) m/e 342 (M+H)+.

Aufarbeitung

  1. washwashed sequentially with 2M sodium carbonate (10 mL), water (20 mL), and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 30-100% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-05ea6e9fe2f147578a0fce98b748e8c6
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720338B2

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