Triethylamine → [(4-Hydroxy-6,7-dimethyl-2-oxo-2H-chromene-3-carbonyl)-amino]-acetic acid ethyl ester

HRID 2190918Notes

Reaction equation

HRID 2190918 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:13])=[C:9]([CH3:12])[CH:10]=2)[O:5][C:4](=[O:14])[CH:3]=1.C(N(CC)CC)C.[CH2:22]([O:24][C:25](=[O:30])[CH2:26][N:27]=[C:28]=[O:29])[CH3:23]>C(Cl)Cl>[CH2:22]([O:24][C:25](=[O:30])[CH2:26][NH:27][C:28]([C:3]1[C:4](=[O:14])[O:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][C:9]([CH3:12])=[C:8]([CH3:13])[CH:7]=2)=[O:29])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76283Ethyl isocyanatoacetateHCID 546820884-Hydroxy-6,7-dimethylcoumarin

Product 1

HCID 86649467[(4-Hydroxy-6,7-dimethyl-2-oxo-2H-chromene-3-carbonyl)-amino]-acetic acid ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Hydroxy-6,7-dimethyl-chromen-2-one (500 mg, 2.4 mmol), triethylamine (368 uL, 2.64 mmol) and methylene chloride (4 mL) were placed together in a dry flask. Isocyanato-acetic acid ethyl ester (283 uL, 2.52 mmol) was added and the reaction was stirred overnight (24 h) at room temperature. The crude reaction mixture was purified using silica gel chromatography (SGC) (1% Methanol in Methylene Chloride) to provide the title compound in 85% yield. MS ESI(−) m/e: 318.33 (M−1).

Workup

  1. customThe crude reaction mixture
  2. customwas purified

Sources & evidence

ORD record
ord-b55f3ac415ce4b37ab7eee5952eec88d
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

Loading…