Hexachloroethane → tert-butyl [(1S)-2-{[5-(5-hydroxy-1,3-benzoxazol-2-yl)isoxazol-3-yl]oxy}-1-methylethyl]carbamate

HRID 1026209Notes

Reaction equation

HRID 1026209 reaction equation
C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl.O[C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][C:37]=1[NH:43][C:44]([C:46]1[O:50][N:49]=[C:48]([O:51][CH2:52][C@@H:53]([NH:55][C:56](=[O:62])[O:57][C:58]([CH3:61])([CH3:60])[CH3:59])[CH3:54])[CH:47]=1)=[O:45]>C(#N)C.O>[OH:42][C:39]1[CH:40]=[CH:41][C:36]2[O:45][C:44]([C:46]3[O:50][N:49]=[C:48]([O:51][CH2:52][C@@H:53]([NH:55][C:56](=[O:62])[O:57][C:58]([CH3:61])([CH3:60])[CH3:59])[CH3:54])[CH:47]=3)=[N:43][C:37]=2[CH:38]=1

Participants

7

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 136372362tert-butyl [(1S)-2-({5-[(2,5-dihydroxyphenyl)carbamoyl]isoxazol-3-yl}oxy)-1-methylethyl]carbamate

Product 1

HCID 86666264tert-butyl [(1S)-2-{[5-(5-hydroxy-1,3-benzoxazol-2-yl)isoxazol-3-yl]oxy}-1-methylethyl]carbamateYield 52.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

Triethylamine (2.83 mL) was added to a solution of triphenylphosphine (2.0 g) and hexachloroethane (1.5 g) in acetonitrile (25 mL), and the mixture was stirred at room temperature for 20 min. To the reaction mixture was further added a solution of tert-butyl [(1S)-2-({5-[(2,5-dihydroxyphenyl)carbamoyl]isoxazol-3-yl}oxy)-1-methylethyl]carbamate (1.0 g) in acetonitrile (5 mL), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, 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 (503 mg).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-98f00c5a2f0a4de0b5a65e8c6ec392cb
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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