Sodium Hydroxide → HCID 131715239, compound

HRID 2308603Notes

Reaction equation

HRID 2308603 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C@@H:4]([CH2:18][NH:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:3]1.[O-:26][C:27]#[N:28].[K+].[OH-].[Na+]>O.Cl>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C@@H:4]([CH2:18][N:19]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:27](=[O:26])[NH2:28])[CH2:3]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 11378442Potassium cyanateHCID 70424265HCID 70424265, compound

Product 1

HCID 131715239HCID 131715239, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8.5 g of 6-methyl-8β-[N-(2-methoxycarbonyl-ethyl)aminomethyl]-ergoline (II: R1 =R2 =R3 =H, R4 =CH3, n=1, A=CH2 --CHR6, R6 =H, B=COOCH3 ; prepared as described in Example 1) and 2.86 g of potassium cyanate in 120 ml of water and 35 ml of 1N hydrochloric acid was heated at 60° C. for one hour. The solution was then neutralized with 1N sodium hydroxide and extracted with chloroform. The organic layer was evaporated off, and the residue was purified by column chromatography on silica gel, to give 6.5 g of the title compound. Rf in ethyl acetate:dimethylformamide:n-butanol:pyridine (4:3:3:1 by volume)=0.45; MS (F.D.): 384 (M+), 352 (M+ --CH3OH).

Workup

  1. customprepared
  2. extractionextracted with chloroform
  3. customThe organic layer was evaporated off
  4. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-30fb2be90a7d45fdab22a3540a10660b
Source dataset
uspto-grants-1987_09
Patent number
US04690929

Reaction notes

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