tert-Butanol → (S)-4-Dibenzofuran-2-yl-4-oxo-2-(2,2,2-trifluoro-acetylamino)-butyric acid tert-butyl ester

HRID 376406Notes

Reaction equation

HRID 376406 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=[O:27])[CH2:15][C@H:16]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[C:17]([OH:19])=[O:18].C(N1C=CN=C1)(N1C=CN=C1)=O.N12CCCN=C1CCCCC2.[C:51](O)([CH3:54])([CH3:53])[CH3:52]>CCOCC.CN(C=O)C>[C:51]([O:18][C:17](=[O:19])[C@@H:16]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:15][C:14]([C:2]1[CH:3]=[CH:4][C:5]2[O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=1)=[O:27])([CH3:54])([CH3:53])[CH3:52]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54131944(S)-4-dibenzofuran-2-yl-4-oxo-2-(2,2,2-trifluoroacetylamino)-butyric acid

Product 1

HCID 54407271(S)-4-Dibenzofuran-2-yl-4-oxo-2-(2,2,2-trifluoro-acetylamino)-butyric acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
24 °C

Procedure

To a DMF solution (10 mL) of (S)-4-dibenzofuran-2-yl-4-oxo-2-(2,2,2-trifluoroacetylamino)-butyric acid (0.3 g, 0.00079 mol) at 40° C. was added carbonyldimidazole (0.13 g, 0.00079 mol). This mixture was stirred for 1 hour and then 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU, 0.12 mL, 0.00079 mol) and t-butanol (0.15 mL, 0.00158 mol) were added. The reaction mixture was stirred for 24 hours at 40° C., cooled to 24° C., and then diluted with ether (20 mL). The solution was washed with water (2×10 mL), brine (2×10 mL), and dried over anhydrous magnesium sulfate. The mixture was filtered and the filtrate was concentrated to an oil by evaporation of the solvent in vacuo. The oil was flash chromatographed on silica gel eluting with 20% ethyl acetate/hexane (v/v) to yield the title compound; mp 92-94° C.

Workup

  1. stirringThe reaction mixture was stirred for 24 hours at 40° C.
  2. washThe solution was washed with water (2×10 mL), brine (2×10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated to an oil by evaporation of the solvent in vacuo
  6. customchromatographed on silica gel eluting with 20% ethyl acetate/hexane (v/v)

Sources & evidence

ORD record
ord-6aa56cf25b95409cb7c154e7c61ac687
Source dataset
uspto-grants-2000_02
Patent number
US06020366

Reaction notes

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