N,N-Dimethylglycine → Tert-butyl 3-(2-(dimethylamino)acetamido)phenylcarbamate

HRID 42270

Reaktionsgleichung

Reaktionsgleichung von HRID 42270
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.[CH3:16][N:17]([CH3:22])[CH2:18][C:19](O)=[O:20].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[CH3:16][N:17]([CH3:22])[CH2:18][C:19]([NH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1)=[O:20]

Komponenten

6

Edukt 3

HCID 673N,N-DimethylglycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

Produkt 1

HCID 68760351Tert-butyl 3-(2-(dimethylamino)acetamido)phenylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 250 mL round bottom flask with stir bar was charged with tert-butyl 3-aminophenylcarbamate (5.315 g, 25.5 mmol), 2-(dimethylamino)acetic acid (2.94 g, 28.5 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (5.17 g, 27.0 mmol) and 4-dimethylaminopyridine (0.09 g, 0.737 mmol) in dichloromethane (100 ml). The solution was stirred at ambient temperature for 2 hours. The reaction mixture was washed into a separatory funnel with an additional 100 mL dichloromethane and washed with 100 mL saturated sodium bicarbonate. The organics were dried over magnesium sulfate, filtered, and concentrated to provide the title compound. MS ESI+) m/e 294.0 (M+H)+.

Aufarbeitung

  1. stirringThe solution was stirred at ambient temperature for 2 hours
  2. washThe reaction mixture was washed into a separatory funnel with an additional 100 mL dichloromethane
  3. washwashed with 100 mL saturated sodium bicarbonate
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7b9a270aaf0b4052bc7356816a3003de
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536180B2

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