Water → HCID 22261901, compound

HRID 1610527Notes

Reaction equation

HRID 1610527 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)O)C(O)=O)=[CH:4][C:3]=1[O:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.C([N:48]([CH2:51]C)CC)C.[OH2:53]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH:13]([C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[O:53][C:51](=[O:36])[NH:48]2)=[CH:4][C:3]=1[O:22][C:23]([F:27])([F:28])[CH:24]([F:26])[F:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 17862137HCID 17862137, compound

Product 1

HCID 22261901HCID 22261901, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-2-((4-chloro-3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-3-(4-fluorophenyl)-3-hydroxypropionic acid (2.0 g, 4.71 mmol) in tetrahydrofuran (40 ml) were added diphenylphosphoryl azide (1.12 ml, 5.18 mmol) and triethylamine (0.99 ml, 7.07 mmol), and the mixture was heated under reflux for 3 hrs. The reaction solution was allowed to cool and water (200 ml) was added. The mixture was extracted with ethyl acetate (200 ml×2). The extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give (4RS,5SR)-4-((4-chloro-3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-5-(4-fluorophenyl)-1,3-oxazolidin-2-one (1.72 g, 87%) as a colorless oil. IR ν maxKBrcm−1: 1759, 1514, 1489. Anal. Calcd for C18H13ClF5NO3: C, 51.26; H, 3.11; N, 3.32. Found: C, 51.16; H, 3.13; N, 3.24. 1H-NMR (CDCl3)δ: 2.30 (2H, d, J=6.8 Hz), 4.25 (1H, q, J=6.8 Hz), 5.30 (1H, brs), 5.80 (1H, d, J=8.0 Hz), 5.98 (1H, tt, J=53.0, 3.0 Hz), 6.89 (1H, dd, J=8.0, 2.0 Hz), 6.99 (1H, s), 7.06-7.20 (2H, m), 7.30-7.42 (3H, m).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. temperatureto cool
  4. extractionThe mixture was extracted with ethyl acetate (200 ml×2)
  5. washThe extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ae2a933550ad4d81825b6df6591d4503
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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