Triphenylphosphine → HCID 86731246, compound

HRID 2277187Notes

Reaction equation

HRID 2277187 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([F:12])=[CH:10][C:9]([C:13]3[O:14][C:15]4[C:21]([F:22])=[C:20]([OH:23])[CH:19]=[CH:18][C:16]=4[N:17]=3)=[C:8]([F:24])[CH:7]=2)[CH2:3][CH2:2]1.O[CH2:26][C@@H:27]([NH:29][C:30](=[O:36])OC(C)(C)C)[CH3:28].[C:37]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[C:11]([F:12])=[CH:10][C:9]([C:13]3[O:14][C:15]4[C:21]([F:22])=[C:20]([O:23][CH2:26][C@@H:27]([NH:29][C:30](=[O:36])[CH3:37])[CH3:28])[CH:19]=[CH:18][C:16]=4[N:17]=3)=[C:8]([F:24])[CH:7]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 66880968DIAD tolueneHCID 86731244HCID 86731244, compound

Product 1

HCID 86731246HCID 86731246, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(cyclopropylmethoxy)-2,5-difluorophenyl)-7-fluoro-1,3-benzoxazol-6-ol (1.34 g), tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (1.05 g) and triphenylphosphine (1.57 g) in THF (50 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 3.16 mL) at 0° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate). To the obtained solid was added 4 M hydrogen chloride/ethyl acetate (10 mL), and the mixture was stirred at room temperature for 10 min, and concentrated. To the residue were added pyridine (10 mL) and acetic anhydride (10 mL), and the mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (704 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)
  3. additionTo the obtained solid was added 4 M hydrogen chloride/ethyl acetate (10 mL)
  4. stirringthe mixture was stirred at room temperature for 10 min
  5. concentrationconcentrated
  6. additionTo the residue were added pyridine (10 mL) and acetic anhydride (10 mL)
  7. stirringthe mixture was stirred at room temperature for 15 min
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6ed56b73c2d44efebd7eef707e0c6a98
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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