Hydrochloric Acid → HCID 59486419, compound

HRID 32105Notes

Reaction equation

HRID 32105 reaction equation
[N:1]([CH:4]1[CH2:13][CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([O:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])[CH:7]=[CH:6][C:5]1=2)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.Cl>C1COCC1>[NH2:1][CH:4]1[CH2:13][CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([O:14][S:15]([C:18]([F:21])([F:19])[F:20])(=[O:17])=[O:16])[CH:7]=[CH:6][C:5]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 72440623Trifluoromethanesulfonic acid 5-azido-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 59486419HCID 59486419, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of trifluoro-methanesulfonic acid 5-azido-5,6,7,8-tetrahydro-naphthalen-2-yl ester (Step C, 10.3 g, 32.1 mmol, 1.0 eq) in THF (70 mL) was added PPh3 (Aldrich, 8.4 g, 32.1 mmol, 1.0 eq), and H2O (30 mL) at 0° C. The mixture was warmed to RT and stirred overnight. 2 N HCl was added until the mixture was acidic (pH ˜1-2). The mixture was extracted with toluene (3×100 mL). The aqueous phase was neutralized with 5 N NaOH to pH around 12-13, and extracted with ether (3×150 mL). The ether solution was dried over Na2SO4 filtered and concentrated in vacuo. The crude was purified by flash chromatography (6% MeOH—CH2Cl2) to provide the title compound.

Workup

  1. extractionThe mixture was extracted with toluene (3×100 mL)
  2. extractionextracted with ether (3×150 mL)
  3. dry with materialThe ether solution was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by flash chromatography (6% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-c78c7ed0ccd842069e92faebcd2e1528
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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