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

HRID 2391042Notes

Reaction equation

HRID 2391042 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
80 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (2.0 g, 7.09 mmol) and triethylamine (0.99 mL, 7.09 mmol) were dissolved in toluene (50 mL). Diphenylphosphoryl azide (1.5 mL, 7.09 mmol) was added, followed by (R)-(+)-1-phenylethyl alcohol (0.865 g, 7.09 mmol; commercially available or prepared using procedures described herein or in the literature: e.g. E. J. Corey et al. J. Am. Chem. 1987, 109, 5551-5553), and the reaction was stirred at 80° C. for 4 hours. The mixture was concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. customcommercially available or prepared
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-16bf6d0ce4dd44288739f885dc35f80c
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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