Hydrochloric Acid → ((R)-2-carbamoyl-propyl)-carbamic acid tert-butyl ester

HRID 246125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246125
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([CH3:14])[C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:16](C)CCCN=C=NCC.ON1C(=O)CCC1=O.[OH-].[NH4+].Cl>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C@H:10]([C:11](=[O:12])[NH2:16])[CH3:14])([CH3:4])([CH3:3])[CH3:2]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 11041840(R)-3-((tert-butoxycarbonyl)amino)-2-methylpropanoic acid

Produkt 1

HCID 22845901((R)-2-carbamoyl-propyl)-carbamic acid tert-butyl esterAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(R)-3-(tert-Butoxycarbonylamino)-2-methylpropanoic acid (465 mg, 2.3 mmol) was dissolved in dichloromethane (11 ml). 4-Dimethylaminopyridine (280 mg, 2.3 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (877 mg, 4.58 mmol) were added, followed by N-hydroxysuccinimide (290 mg, 2.52 mmol). After 4 h of stirring at room temperature, concentrated ammonium hydroxide (1.6 ml) was added slowly. The reaction mixture was stirred for an additional 20 min then aqueous HCl and ethyl acetate were added and the aqueous layer was extracted six times with ethyl acetate. The combined organic layers were washed with sodium bicarbonate solution and dried over sodium sulfate. After evaporation, the residue was purified by silica gel chromatography to give 335 mg (72%) of ((R)-2-carbamoyl-propyl)-carbamic acid tert-butyl ester. (M+Na)+=225.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for an additional 20 min
  2. extractionthe aqueous layer was extracted six times with ethyl acetate
  3. washThe combined organic layers were washed with sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation
  6. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f28b6b3edde042c796bb9ce5b567ae25
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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