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

HRID 553711Notes

Reaction equation

HRID 553711 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-ec32ca20097f4a5f9d304a060bc8fe8a
Source dataset
uspto-grants-2011_11
Patent number
US08048902B2

Reaction notes

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