Triethylamine → [Methyl-(4-nitro-benzoyl)-amino]-acetic acid methyl ester

HRID 2235828Notes

Reaction equation

HRID 2235828 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH3:14][O:15][C:16](=[O:20])[CH2:17][NH:18][CH3:19].C(N(CC)CC)C>C(Cl)Cl>[CH3:14][O:15][C:16](=[O:20])[CH2:17][N:18]([CH3:19])[C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)

Product 1

HCID 11334229[Methyl-(4-nitro-benzoyl)-amino]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitro-benzoyl chloride (1.396 g; 7.52 mmol), methylamino-acetic acid methyl ester hydrochloride (1.264 g; 9.06 mmol) and triethyl-amine (2.40 mL; 17.2 mmol) were reacted in DCM (35 mL). After 2 days the r×n was washed with water (1×10 mL), 1 M HCl (2×10 mL), water (1×10 mL) and satd NaHCO3 (2×10 mL). After drying over MgSO4, filtration through silica with a 10:1 DCM:i-PrOH wash and concd, the product was purified by MPLC (silica; 0-->10% i-PrOH in DCM gradient) yielding a pale yellow-orange solid (1.394 g; 73%) as a mix of rotamers. 1H NMR (CDCl3; major rotamer) δ 8.31 (m, 2H), 7.66 (m, 2H), 4.31 (s, 2H), 3.82 (s, 3H), 3.03 (s, 3H).

Workup

  1. washAfter 2 days the r×n was washed with water (1×10 mL), 1 M HCl (2×10 mL), water (1×10 mL) and satd NaHCO3 (2×10 mL)
  2. dry with materialAfter drying over MgSO4, filtration through silica with a 10:1 DCM
  3. washi-PrOH wash
  4. customconcd, the product was purified by MPLC (silica; 0-->10% i-PrOH in DCM gradient)
  5. customyielding a pale yellow-orange solid (1.394 g; 73%) as
  6. additiona mix of rotamers

Sources & evidence

ORD record
ord-e255b4879c0543b29ff24e1804fe8fc8
Source dataset
uspto-grants-2010_05
Patent number
US07714022B2

Reaction notes

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