Acetonitrile--water (1/1) → HCID 57457165, compound

HRID 2354381Notes

Reaction equation

HRID 2354381 reaction equation
CC([O:5][C:6](=[O:24])[CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=[CH:17][C:12]=2[O:11][CH2:10][C:9]1=[O:23])(C)C.CC#N.O>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:21]([O:20][C:18]([C:15]1[CH:16]=[CH:17][C:12]2[O:11][CH2:10][C:9](=[O:23])[N:8]([CH2:7][C:6]([OH:24])=[O:5])[C:13]=2[CH:14]=1)=[O:19])[CH3:22]

Participants

5

Reactant 2

HCID 18373917Acetonitrile--water (1/1)HCID 57457149HCID 57457149, compound

Product 1

HCID 57457165HCID 57457165, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

Ethyl 4-{2-[(1,1-dimethylethyl)oxy]-2-oxoethyl}-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (6.14 g, 18.0 mmol) was dissolved in 60 mL of a 1:1 solution of methylene chloride and trifluoroacetic acid. The mixture was allowed to stir at room temperature for three hours before it was determined to be complete by HPLC (Eclipse XDB-C18, 4.6×250 mm, 5 micron, 1-99% CH3CN/H2O with 0.1% trifluoroacetic acid). The chromatogram indicated that all of the starting material (Rt=7.7 min) was consumed and converted to the desired product (Rt=5.3 min). The volatiles were removed by rotary evaporation and the resulting residue was taken up in a minimal amount of methylene chloride and treated with a 2 M solution of hydrochloric acid in ethyl ether. After allowing the mixture to stir for several minutes, the mixture was concentrated once again by rotary evaporation to yield {6-[(ethyloxy)carbonyl]-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl}acetic acid (5.28 g, 17.9 mmol, 99%) as a brown amorphous solid. MS (ES) m/e 280 [M+H]+.

Workup

  1. customwas consumed
  2. customThe volatiles were removed by rotary evaporation
  3. additiontreated with a 2 M solution of hydrochloric acid in ethyl ether
  4. stirringto stir for several minutes
  5. concentrationthe mixture was concentrated once again by rotary evaporation

Sources & evidence

ORD record
ord-40975aaf5ae04bdaa76cc64ad45f36f6
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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