Water → HCID 59496620, Verbindung

HRID 449440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449440
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][CH:7]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:8][C:9]([OH:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].O.O1CCCC1>>[CH:12]1([CH:7]([NH:6][C:2]([O:4][CH3:5])=[O:3])[CH2:8][C:9]([OH:11])=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

6

Edukt 5

HCID 962WaterHCID 6586Methyl chloroformateHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 2733681beta-Aminocyclohexanepropanoic acid

Produkt 1

HCID 59496620HCID 59496620, VerbindungAusbeute 97,1 %

Versuchsvorschrift

Methyl chloroformate (54 uL, 0.70 mmol) was added to a mixture of 3-amino-3-cyclohexylpropanoic acid (100.0 mg, 0.5840 mmol) (Key Organics/Bionet, Cat. #7T-0112) and potassium carbonate (160 mg, 1.2 mmol) in water (2.0 mL, 110 mmol) and tetrahydrofuran (2.0 mL, 25 mmol). After stirring at r.t. for 10 min, the mixture was extracted with ether to remove impurity. The aqueous layer was adjusted to pH=2 with HCl, and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to afford the desired product (130 mg, 97%). Analytic LCMS (M+H)+: m/z=230.1.

Aufarbeitung

  1. extractionthe mixture was extracted with ether
  2. customto remove impurity
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bc634a5758574bf798c8210d5c416cda
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481732B2

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