Pyridine → HCID 86748783, compound

HRID 1647561Notes

Reaction equation

HRID 1647561 reaction equation
[CH2:1]([N:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[P:28](Cl)(=[O:43])([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([N:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:9]([C:12]([OH:14])=[O:13])[CH2:10][O:11][P:28]([O:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([O:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:43])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 75654Diphenyl chlorophosphateHCID 22867308HCID 22867308, compound

Product 1

HCID 86748783HCID 86748783, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 30 ml of dried methylene chloride was dissolved 3.75 g of benzyl N-t-butoxycarbonyl-D-serine, and 1.23 ml of pyridine, 1.86 g of 4-dimethylaminopyridine, and 4.09 g of diphenyl phosphorochloridate were successively added thereto at room temperature, followed by stirring at that temperature for 3 hours. The reaction mixture was washed successively with 1N hydrochloric acid and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: 2% acetone-containing chloroform) to obtain 5.38 g of benzyl N-t-butoxycarbonyl-O-diphenylphosphono-D-serine as a white solid.

Workup

  1. additionwere successively added
  2. customat room temperature
  3. washThe reaction mixture was washed successively with 1N hydrochloric acid
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: 2% acetone-containing chloroform)

Sources & evidence

ORD record
ord-c99ba8d2b451408e82e5d20b56e4447b
Source dataset
uspto-grants-1995_07
Patent number
US05432267

Reaction notes

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