Ethyl Acetate → HCID 21941645, compound

HRID 2216295Notes

Reaction equation

HRID 2216295 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:34]([O-])=O)[C:5]([OH:33])=[C:6]([C:8]([CH3:32])([CH3:31])[CH2:9][C:10]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[C:22](=[O:23])[O:21][N:20]=[C:19]([CH3:24])[C:18]=3[CH:25]=2)=[O:12])[CH:7]=1.[CH2:37](OC(OCC)OCC)C.C(OCC)(=O)C>O1CCCC1.C(O)(=O)C.[Fe]>[F:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:31])([CH3:32])[CH2:9][C:10]([OH:30])([C:26]([F:29])([F:27])[F:28])[C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[C:22](=[O:23])[O:21][N:20]=[C:19]([CH3:24])[C:18]=3[CH:25]=2)=[O:12])[C:5]2[O:33][CH:37]=[N:34][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 31214Ethyl orthoformateHCID 21941655HCID 21941655, compound

Product 1

HCID 21941645HCID 21941645, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

103 mg of (−)-6-[4-(5-fluoro-2-hydroxy-3-nitrophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)valeroyl-amino]-4-methyl-2,3-benzoxazin-1-one in 5 ml of tetrahydrofuran and 1 ml of acetic acid are stirred for 2.5 hours with 300 mg of iron, mixed with 0.5 ml of orthoformic acid triethyl ester and ethyl acetate, suctioned off and concentrated by evaporation after standing for 4 hours at room temperature. The residue is dissolved in ethyl acetate and mixed with 0.05 ml of orthoformic acid. After 20 hours at room temperature, 72 mg of (+)-6-[4-(5-fluorobenzoxazol-7-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)valeroylamino]-4-methyl-2,3-benzoxazin-1-one is suctioned off. MS, flash point 276–277° C., (+)-enantiomer with [α]D+53.0° (c=0.25, THF).

Workup

  1. concentrationconcentrated by evaporation
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. additionmixed with 0.05 ml of orthoformic acid
  4. waitAfter 20 hours at room temperature

Sources & evidence

ORD record
ord-26dbbed1592b4059b3fe65eb88d71c0f
Source dataset
uspto-grants-2006_09
Patent number
US07112584B2

Reaction notes

Loading…