2-Methoxyethanol → HCID 66815747, compound

HRID 1697098Notes

Reaction equation

HRID 1697098 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:20](=[O:29])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]([N:8]([C:15](=[O:19])[C:16](Cl)=[O:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[CH3:30][O:31][CH2:32][CH2:33][OH:34].CCN(CC)CC>C1COCC1>[CH3:30][O:31][CH2:32][CH2:33][O:34][C:16](=[O:17])[C:15]([N:8]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[C:20](=[O:29])[CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:19]

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 8471TriethylamineHCID 86624857HCID 86624857, compound

Product 1

HCID 66815747HCID 66815747, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of {[5-fluoro-2-(3-phenyl-propionyl)-phenyl]-phenyl-amino}-oxo-acetyl chloride (540 mg) in THF (3 mL) was added 2-methoxyethanol (0.12 mL), followed by Et3N (0.22 mL). The reaction mixture became a pale yellow slurry: additional THF (2 mL) was added, and the mixture allowed to stand for 1 h. The mixture was then quenched with NH4Cl (sat'd aq), extracted with EtOAc, washed with brine, and concentrated to yield N-[5-fluoro-2-(3-phenyl-propionyl)-phenyl]-N-phenyl-oxalamic acid 2-methoxy-ethyl ester (504 mg) as an oil.

Workup

  1. customThe mixture was then quenched with NH4Cl (sat'd aq)
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-360b218adf104dfa8dde9c5b78ec928d
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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