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Triethylamine → [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid 1-(2-fluoro-phenyl)-ethyl ester

HRID 2092430
Notes
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Reaction equation

HRID 2092430 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.[F: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>[F: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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1230662-Fluoro-alpha-methylbenzenemethanolHCID 199401P,P-Diphenylphosphinic azideHCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 67352942[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid 1-(2-fluoro-phenyl)-ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (4 g, 14.2 mmol) was dissolved in toluene (150 mL). Triethylamine (2.187 mL, 15.6 mmol) was added, followed by diphenylphosphoryl azide (3.372 mL, 15.6 mmol), and the mixture was stirred for 10 minutes. 2-Fluoro-alpha-methylbenzyl alcohol (2 g, 15.6 mmol) was added, and the reaction was stirred at 80° C. overnight. The mixture was cooled to room temperature and concentrated, and the residue was partitioned between with EtOAc and water. The organic layer was washed 4 times with water and once with brine, and then dried, filtered, and concentrated, and the residue was purified by silica gel chromatography (dry load; 0-100% EtOAc in hexanes) to give [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid 1-(2-fluoro-phenyl)-ethyl ester.

Workup

  1. stirringthe reaction was stirred at 80° C. overnight
  2. concentrationconcentrated
  3. customthe residue was partitioned between with EtOAc and water
  4. washThe organic layer was washed 4 times with water
  5. dry with materialonce with brine, and then dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel chromatography (dry load; 0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-22dba9e2a7204fb5b11ab70f8b45a935
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440707B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes