Acetic Acid → (S)-3-methyl-4-oxo-4-(2-phenyl-benzoxazol-6-yl)-butyric acid

HRID 1619940Notes

Reaction equation

HRID 1619940 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.C([Li])CCC.[CH3:22][C@H:23]1[CH2:27][C:26](=[O:28])[O:25][C:24]1=[O:29].C(O)(=O)C>C1COCC1.CCCCCC>[CH3:22][C@H:23]([C:24](=[O:29])[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1)[CH2:27][C:26]([OH:28])=[O:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 642778(3S)-3-methyloxolane-2,5-dioneHCID 230259476-Bromo-2-phenylbenzo[d]oxazoleHCID 178418339Butyllithium

Product 1

HCID 67462340(S)-3-methyl-4-oxo-4-(2-phenyl-benzoxazol-6-yl)-butyric acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

400 mg (1.46 mmol) 6-bromo-2-phenyl-benzoxazole are dissolved in 15 ml THF and cooled to −70° C., and 1.22 ml (1.92 mmol) n-butyl lithium 1.6M in hexane are added dropwise. This solution chilled to −70° C. is added dropwise to an equally cold −70° C. solution of 220 mg (1.93 mmol) (S)-3-methyl-dihydro-furan-2,5-dione and 15 ml THF. After 15 min stirring the mixture is poured onto semisaturated, acetic acid-containing saline solution and extracted with EA. The org. phase is concentrated by rotary evaporation i. V. and the residue is separated through silica gel (eluant DCM/EA/glacial acetic acid).

Workup

  1. temperatureThis solution chilled to −70° C.
  2. additionis poured
  3. extractionextracted with EA
  4. concentrationphase is concentrated by rotary evaporation i
  5. customand the residue is separated through silica gel (eluant DCM/EA/glacial acetic acid)

Sources & evidence

ORD record
ord-766c81a9031c466e99a2301aa44cd0c3
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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