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

HRID 42270

Reaction equation

HRID 42270 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-7b9a270aaf0b4052bc7356816a3003de
Source dataset
uspto-grants-2013_09
Patent number
US08536180B2

Linked notes

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