Triethylamine → HCID 22261382, compound

HRID 1610664Notes

Reaction equation

HRID 1610664 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH:7]([OH:26])[CH:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:25])([F:24])[CH:21]([F:23])[F:22])[CH:14]=2)C(O)=O)=[CH:4][CH:3]=1.C([N:29]([CH2:32]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:41])C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[S:6][C:5]([CH:7]2[O:26][C:32](=[O:41])[NH:29][CH:8]2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:24])([F:25])[CH:21]([F:22])[F:23])[CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261781HCID 22261781, compound

Product 1

HCID 22261382HCID 22261382, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(5-chloro-2-thienyl)-3-hydroxy-2-[3-(1,1,2,2 tetrafluoroethoxy)benzyl]propionic acid (8.996 g, 21.79 mmol) in tetrahydrofuran (80 ml) were added triethylamine (3.65 ml, 26.2 mmol) and diphenylphosphoryl azide (6.60 g, 24.0 mmol), and the mixture was heated under reflux overnight. The solvent of the reaction solution was evaporated under reduced pressure and the obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1-1/1) to give the objective substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customThe solvent of the reaction solution was evaporated under reduced pressure
  4. customthe obtained crude product
  5. customwas purified by silica gel column chromatography (hexane/ethyl acetate=3/1-1/1)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-192d5ee076c14c2197854fe06ff488f5
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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