Triethylamine → HCID 22261568, compound

HRID 1610719Notes

Reaction equation

HRID 1610719 reaction equation
[C:1]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][CH:10]([CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[OH:15])C(O)=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([N:27]([CH2:30]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1>O1CCCC1>[C:1]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][CH:10]2[CH:14]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[O:15][C:30](=[O:39])[NH:27]2)=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261597HCID 22261597, compound

Product 1

HCID 22261568HCID 22261568, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-2-[4-(tert-butyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid (5.07 g, 15.3 mmol) in tetrahydrofuran (150 ml) were added triethylamine (3.2 ml, 22.95 mmol) and diphenylphosphoryl azide (3.63 ml, 16.8 mmol) at room temperature, and the mixture was heated under reflux for 5 hrs. The solvent was evaporated, passed through silica gel column, and purified by recrystallization (hexane-ethyl acetate) to give (4RS,5SR)-4-[4-(tert-butyl)benzyl]-5-(4-fluorophenyl)-1,3-oxazolidin-2-one (3.98 g, 79%) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. customThe solvent was evaporated
  4. custompurified by recrystallization (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1b611a8301db49ff9d1256bc48bd3d97
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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