Tetrahydrofuran → HCID 86731189, compound

HRID 2277136Notes

Reaction equation

HRID 2277136 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:23]=[C:22]([O:24][CH2:25][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:27])[CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:11][C:10]=1[F:36])[C:2]1[CH:7]=CC=CC=1.C1C[O:40]CC1>[C].[Pd]>[F:36][C:10]1[CH:11]=[C:12]([C:15]2[O:16][C:17]3[CH:23]=[C:22]([O:24][CH2:25][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:27])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2](=[O:40])[CH3:7]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86731190HCID 86731190, compound

Product 1

HCID 86731189HCID 86731189, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

A mixture of tert-butyl ((2S)-1-((2-(4-(benzyloxy)-3-fluorophenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)carbamate (4.26 g), 10% palladium-carbon (containing water (50%), 0.920 g) and THF (40 mL) was stirred at room temperature for 1 hr and min under a hydrogen atmosphere. The catalyst was removed by filtration, and the obtained filtrate was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate, and the solution was subjected to silica gel chromatography (ethyl acetate), and the solvent was evaporated. To a solution of the obtained residue in DMF (40 mL) were added potassium carbonate (1.32 g) and bromoacetone (0.888 mL), and the mixture was stirred overnight at 60° C. The reaction mixture was diluted with ethyl acetate, and washed with saturated brine, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (4.67 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in ethyl acetate
  4. customthe solvent was evaporated
  5. additionTo a solution of the obtained residue in DMF (40 mL) were added potassium carbonate (1.32 g) and bromoacetone (0.888 mL)
  6. stirringthe mixture was stirred overnight at 60° C
  7. additionThe reaction mixture was diluted with ethyl acetate
  8. washwashed with saturated brine
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3c85100e810f4cc8a392b5bb27a2f49e
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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