Triethylamine → (1R)-1-Phenylethyl N-(5-(4-bromophenyl)-3-methyl-4-isoxazolyl)carbamate

HRID 2092457Notes

Reaction equation

HRID 2092457 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.[C:41]1([C@H:47]([OH:49])[CH3:48])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1(C)C=CC=CC=1>[C:41]1([C@H:47]([O:49][C:22](=[O:31])[NH:19][C:9]2[C:10]([CH3:13])=[N:11][O:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH3:48])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6375161-Phenylethanol, (R)-HCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 66660383(1R)-1-Phenylethyl N-(5-(4-bromophenyl)-3-methyl-4-isoxazolyl)carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (25 g, 88.7 mmol) in toluene (500 mL) was added triethylamine (18.5 mL, 133 mmol), followed by diphenylphosphoryl azide (22.1 mL, 101.9 mmol). (R)-(+)-1-Phenylethyl alcohol (11.9 mL, 97.5 mmol) was added, and the reaction was stirred at 75° C. for 2 hours. The mixture was partitioned between EtOAc and H2O and filtered through Celite. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. filtrationfiltered through Celite
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2790ba5cefce41939ae2299a72736df2
Source dataset
uspto-grants-2013_05
Patent number
US08440707B2

Reaction notes

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