Water → HCID 86731298, compound

HRID 2277228Notes

Reaction equation

HRID 2277228 reaction equation
[N:1]([CH:4]([CH3:28])[CH2:5][O:6][CH:7]1[CH2:27][CH2:26][C:10]2[N:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]4[CH2:24][CH2:23]4)=[C:16]([Cl:25])[CH:15]=3)[O:13][C:9]=2[CH2:8]1)=[N+]=[N-].C1(P([C:42]2[CH:47]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH2:48]>C1COCC1>[Cl:25][C:16]1[CH:15]=[C:14]([C:12]2[O:13][C:9]3[CH2:8][CH:7]([O:6][CH2:5][CH:4]([NH:1][C:47](=[O:48])[CH3:42])[CH3:28])[CH2:27][CH2:26][C:10]=3[N:11]=2)[CH:19]=[CH:18][C:17]=1[O:20][CH2:21][CH:22]1[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86731299HCID 86731299, compound

Product 1

HCID 86731298HCID 86731298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-(2-azidopropoxy)-2-(3-chloro-4-(cyclopropylmethoxy)phenyl)-4,5,6,7-tetrahydro-1,3-benzoxazole (6.08 g) in THF (30 mL) were added triphenylphosphine (4.75 g) and water (5 mL), and the mixture was stirred overnight at 60° C. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate). To the obtained oil were added pyridine (10 mL) and acetic anhydride (10 mL), and the mixture was stirred at room temperature for 10 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol) to give the title compound (3.02 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)
  3. additionTo the obtained oil were added pyridine (10 mL) and acetic anhydride (10 mL)
  4. stirringthe mixture was stirred at room temperature for 10 min
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-b8ee7f0e135c4f6d87f3f721916ac7d0
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

Loading…