Triethylamine → HCID 22262120, compound

HRID 1610621Notes

Reaction equation

HRID 1610621 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:28])[CH:9]([CH2:13][C:14]2[CH:27]=[CH:26][C:17]3[O:18][C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[O:21][C:16]=3[CH:15]=2)C(O)=O)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.C([N:48]([CH2:51]C)CC)C>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:28][C:51](=[O:36])[NH:48][CH:9]2[CH2:13][C:14]2[CH:27]=[CH:26][C:17]3[O:18][C:19]([F:24])([F:25])[C:20]([F:23])([F:22])[O:21][C:16]=3[CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261525HCID 22261525, compound

Product 1

HCID 22262120HCID 22262120, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methyl]propanoic acid (3.3 g, 8.16 mmol) in tetrahydrofuran (120 ml) were added diphenylphosphoryl azide (1.94 ml, 8.98. mmol) and triethylamine (1.71 ml, 12.2 mmol), and the mixture was heated under reflux for 1 hr. The reaction solution was allowed to cool and the mixture was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate). Recrystallization from ethyl acetate-hexane gave the objective substance (2.74 g, 84%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureto cool
  4. customthe mixture was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  6. customRecrystallization from ethyl acetate-hexane
  7. customgave the objective substance (2.74 g, 84%)

Sources & evidence

ORD record
ord-3ac0603658c24683aedbc091c78a9c4d
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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