Lithium hydroxide, monohydrate → 3-[3-(1,2-benzisoxazol-3-ylmethyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]hexanoic acid

HRID 1747358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747358
C([O:3][C:4](=[O:30])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][N:21]=2)[C:11]1=[O:29])[CH2:7][CH2:8][CH3:9])C.O.[OH-].[Li+]>C1COCC1.O>[O:22]1[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:20]([CH2:19][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:30])=[O:3])[C:11]2=[O:29])=[N:21]1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 594973183-(3-1,2-Benzisoxazol-3-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl ester

Produkt 1

HCID 594973363-[3-(1,2-benzisoxazol-3-ylmethyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]hexanoic acidAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-(3-1,2-benzisoxazol-3-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl ester (70 mg, 0.17 mmol) in THF (5 ml) and water (0.5 ml) was added lithium hydroxide monohydrate (22 mg, 0.52 mmol). Upon complete consumption of the starting material, the reaction was concentrated to low volume and diluted with water (20 ml) and acetic acid (0.5 ml). The resulting heterogeneous mixture was stirred for 1 h after which time the precipitated product was collected via filtration. The solid was washed with water and dried on house vacuum at 40° C. (18 h, over P2O5) to give 52 mg (80%) of the desired product. LCMS (ESMS): m/z 380.41 (M+H+).

Aufarbeitung

  1. customUpon complete consumption of the starting material
  2. concentrationthe reaction was concentrated to low volume
  3. additiondiluted with water (20 ml) and acetic acid (0.5 ml)
  4. filtrationwas collected via filtration
  5. washThe solid was washed with water
  6. dry with materialdried on house vacuum at 40° C. (18 h, over P2O5)

Quellen und Nachweise

ORD-Eintrag
ord-14f0d0e5e1cb4abebf0b04882c5f81f0
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150556B2

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