2-Naphthol → HCID 53327511, compound

HRID 1465996Notes

Reaction equation

HRID 1465996 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[N:13]=[CH:14][S:15][CH:16]=2)=[O:9])[CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][C:37]=1O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1.O>[CH:44]1[C:45]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:41]=[CH:42][C:43]=1[O:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[N:13]=[CH:14][S:15][CH:16]=2)=[O:9])[CH2:4]1

Participants

7

Reactant 4

HCID 86632-NaphtholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67325214HCID 67325214, compound

Product 1

HCID 53327511HCID 53327511, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

0.25 g (1.03 mmol) of thiazol-4-ylmethyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate is dissolved in 8 ml of toluene. 0.35 g (1.34 mmol) of triphenylphosphine and 0.16 g (1.13 mmol) of naphth-2-ol are added and then the medium is cooled to 0° C. for slow addition of a solution of 0.27 g (1.34 mmol) of diisopropyl azodicarboxylate in 2 ml of toluene. The medium is stirred at ambient temperature for 14 hours. The residue obtained is taken up in water and extracted twice with dichloromethane. The combined organic phases are washed with a saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated under vacuum. The residue is purified by chromatography on silica gel, elution being carried out with a 99/1 to 98/2 mixture of dichloromethane and methanol. 0.15 g of the expected product is obtained in the form of a powder.

Workup

  1. customThe residue obtained
  2. extractionextracted twice with dichloromethane
  3. washThe combined organic phases are washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by chromatography on silica gel, elution
  8. additionbeing carried out with a 99/1 to 98/2 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-88c6d31ff7ec4b488b1fcca708649087
Source dataset
uspto-grants-2015_04
Patent number
US09000010B2

Reaction notes

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