Triethylamine → [5-(4-Bromophenyl)-3-methylisoxazol-4-yl]carbamic acid 1-(2-chlorophenyl)ethyl ester

HRID 1253765Notes

Reaction equation

HRID 1253765 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2C(O)=O)=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[Cl:41][C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[CH:44]([OH:46])[CH3:45]>C1(C)C=CC=CC=1>[Cl:41][C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[CH:44]([O:46][C:22](=[O:31])[NH:19][C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:45]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 260821-(2-Chlorophenyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 67350786[5-(4-Bromophenyl)-3-methylisoxazol-4-yl]carbamic acid 1-(2-chlorophenyl)ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 5-(4-bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (7.0 g, 24.8 mmol) and triethylamine (3.46 g, 24.8 mmol) in toluene (250 mL) was added diphenylphosphoryl azide (5.31 mL, 24.8 mmol), followed by 2-chloro-alpha-methylbenzyl alcohol (3.88 g, 24.8 mmol), and the reaction was stirred at 80° C. for 2.5 hours. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was dissolved in EtOAc and filtered through Celite to remove a precipitate that was present. The crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionthe residue was dissolved in EtOAc
  7. filtrationfiltered through Celite
  8. customto remove a precipitate that
  9. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bbea4e706dc64d4e8e1e4b58199b9687
Source dataset
uspto-grants-2013_06
Patent number
US08455499B2

Reaction notes

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