Pyridine → HCID 10788517, compound

HRID 2184997Notes

Reaction equation

HRID 2184997 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[S:27](Cl)([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:34][C:33]1[CH:35]=[CH:36][C:30]([S:27]([O:14][CH2:13][C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:29])=[O:28])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chloride2×HCID 14802498HCID 14802498, compound

Product 1

HCID 10788517HCID 10788517, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

53.9 g of (R)-2-benzyloxycarbonylamino-2-phenylethanol (198.7 mmol) were dissolved in a mixture of 500 ml of methylene chloride and 80.3 ml (993.5 mmol) of pyridine. 45.5 g (238.4 mmol) of tosyl chloride in 240 ml of methylene chloride were added at 0° C. with stirring and the mixture was stirred at room temperature for 7 hours. A further 11.36 g of tosyl chloride (59.61 mmol) were added. The mixture was stirred at 0° C. for 5 hours. The batch was then allowed to stand overnight at room temperature and concentrated in vacuo. The residue was taken up in ethyl acetate. The organic phase was washed three times with 10% strength aqueous citric acid solution and twice with water, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether, filtered off with suction, washed with diethyl ether and dried over phosphorus pentoxide. Yield: 60.9 g (72%). The mother liquor was concentrated, taken up in n-heptane/ethyl acetate (6/4) and chromatographed on silica gel to give an additional yield of 3.5 g (4.2%).

Workup

  1. stirringthe mixture was stirred at room temperature for 7 hours
  2. stirringThe mixture was stirred at 0° C. for 5 hours
  3. concentrationconcentrated in vacuo
  4. washThe organic phase was washed three times with 10% strength aqueous citric acid solution
  5. dry with materialtwice with water, dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethyl ether
  8. filtrationfiltered off with suction
  9. washwashed with diethyl ether
  10. dry with materialdried over phosphorus pentoxide
  11. concentrationThe mother liquor was concentrated
  12. customchromatographed on silica gel
  13. customto give an additional yield of 3.5 g (4.2%)

Sources & evidence

ORD record
ord-cb8ddf4568a247779e8679b7a3354126
Source dataset
uspto-grants-2002_06
Patent number
US06399643B1

Reaction notes

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