Water → HCID 57827537, compound

HRID 1693242Notes

Reaction equation

HRID 1693242 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]1[CH:22]=[C:23]([C@:27]2([NH:34][C:35]([NH2:37])=[S:36])[CH2:32][CH2:31][O:30][CH2:29][C@@H:28]2O)[CH:24]=[CH:25][CH:26]=1.O>O1CCCC1>[Br:20][C:21]1[CH:22]=[C:23]([C@:27]23[CH2:32][CH2:31][O:30][CH2:29][C@H:28]2[S:36][C:35]([NH2:37])=[N:34]3)[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 57827708HCID 57827708, compound

Product 1

HCID 57827537HCID 57827537, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl azodicarbonate (13.0 mL) was added dropwise to a solution of triphenylphosphine (7.51 g) in tetrahydrofuran (200 mL) in an ice bath. The mixture was warmed to room temperature and stirred for 30 minutes. The reaction solution was cooled to 0° C., and a solution of (±)-[(3R*,4R*)-4-(3-bromophenyl)-3-hydroxytetrahydropyran-4-yl]thiourea (6.33 g) in tetrahydrofuran (44 mL) was added dropwise. The mixture was stirred overnight while gradually warming to room temperature. Water was added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain a crude product. The resulting crude product was purified by silica gel column chromatography again to obtain the title compound (3.55 g).

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. stirringThe mixture was stirred overnight
  3. temperaturewhile gradually warming to room temperature
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. customto obtain a crude product
  8. customThe resulting crude product was purified by silica gel column chromatography again

Sources & evidence

ORD record
ord-e94efb91929f42b799e767663d6bf7a3
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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