Hydrochloric Acid → HCID 10650199, compound

HRID 1645792Notes

Reaction equation

HRID 1645792 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH:7]([CH2:20][S:21]([C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1)(=[O:23])=[O:22])[C:8]([N:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][C:12](O)=[O:13])=[O:9])=[O:4].[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C(P(=O)(OCC)OCC)#N.Cl>CN(C)C=O>[CH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[CH:33][C:24]=1[S:21]([CH2:20][CH:7]([C:8](=[O:9])[N:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][C:12]([N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:13])[CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])(=[O:22])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 76257Diethyl cyanophosphonateHCID 10790794HCID 10790794, compound

Product 1

HCID 10650199HCID 10650199, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-[2-(2-methoxycarbonylethyl)-3-(2-naphthylsulfonyl)propionyl]-N-pentylglycine (0.30 g), piperidine (0.12 ml) in N,N-dimethylformamide (5 ml) was added diethyl cyanophosphonate (0.1 ml) with stirring at 0° C. After stirring at room temperature for 16 hours, a dilute hydrochloric acid was added, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution and water, dried over MgSO4, and evaporated at reduced pressure. The residue was purified by flash column chromatography on silica eluting with chloroform/methanol (20:1) to give 0.18 g of methyl 5-(2-naphthylsulfonyl)-4-(N-pentyl-N-piperidinocarbonylmethylcarbamoyl)pentanoate as oil. ##STR26##

Workup

  1. stirringAfter stirring at room temperature for 16 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium bicarbonate solution and water
  4. dry with materialdried over MgSO4
  5. customevaporated at reduced pressure
  6. customThe residue was purified by flash column chromatography on silica eluting with chloroform/methanol (20:1)

Sources & evidence

ORD record
ord-651d3bb2eec24a28b63d52a73507f3d6
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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