Ethylamine → [3-(4-Ethylcarbamoyl-2-isopropylsulfanylmethyl-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester

HRID 888497Notes

Reaction equation

HRID 888497 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:28][CH3:29])=[C:11]([CH:27]=1)[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][C:14]=1[CH2:22][S:23][CH:24]([CH3:26])[CH3:25])=[O:5])[CH3:2].C(Cl)(=O)C(Cl)=O.[CH2:36]([NH2:38])[CH3:37].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:28][CH3:29])=[C:11]([O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](=[O:19])[NH:38][CH2:36][CH3:37])=[CH:15][C:14]=2[CH2:22][S:23][CH:24]([CH3:26])[CH3:25])[CH:27]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 583727134-(5-Ethoxycarbonylmethyl-2-methoxy-phenoxy)-3-isopropylsulfanylmethyl-benzoic acid

Product 1

HCID 58372766[3-(4-Ethylcarbamoyl-2-isopropylsulfanylmethyl-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To 4-(5-ethoxycarbonylmethyl-2-methoxy-phenoxy)-3-isopropylsulfanylmethyl-benzoic acid (0.07 g, 0.17 mmol) in CH2Cl2 (10 mL) and DMF (1 drop) was added oxalyl chloride (0.04 mL, 0.5 mmol), and the reaction was stirred at room temperature for 30 minutes. After concentrating to dryness, ethylamine (2M in THF; 0.25 mL, 0.5 mmol) was added, followed by CH2Cl2 (10 mL) and diisopropylethylamine (0.5 mL), and the reaction was stirred at room temperature for 15 minutes. The mixture was worked up to give the title compound.

Workup

  1. additionwas added
  2. stirringthe reaction was stirred at room temperature for 15 minutes

Sources & evidence

ORD record
ord-0d6d0d3cdb164a7cb9ae78c7bdbe4b84
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

Loading…