Phosphorus oxychloride → HCID 13863917, compound

HRID 1249102Notes

Reaction equation

HRID 1249102 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:23]([C:24]([NH2:26])=O)[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH:23]([C:24]#[N:26])[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13863915HCID 13863915, compound

Product 1

HCID 13863917HCID 13863917, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(3RS)-2-Benzyloxycarbonyl-1,2,3,4-tetrahydro-β-carboline-3-carboxamide (1.05 g) is dissolved in pyridine (6 ml) and thereto is added dropwise POCl3 (0.37 ml) at -5° C. The mixture is stirred at the same temperature for 2 hours, and the reaction mixture is poured onto ice-water and extracted with ethyl acetate. The ethyl acetate layer is washed with 10% HCl and water and dried, and then the solvent is distilled off to give the title compound (0.81 g, 82%) as white powder.

Workup

  1. additionthe reaction mixture is poured onto ice-water
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer is washed with 10% HCl and water
  4. customdried
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-bbf3b7d1aa184108ae4b06c19922699c
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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