Water → HCID 86742052, compound

HRID 231706Notes

Reaction equation

HRID 231706 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)=[C:13]([C:18]#[C:19][CH2:20][O:21]C2CCCCO2)[NH:12]4)[CH2:5][C@H:4]([NH:28][C:29](=[O:35])[N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[CH2:3]1.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:21][C:20]#[C:19][CH2:18][C:13]1[NH:12][C:11]2[C:17]3[C:14]=1[CH2:15][C@@H:16]1[C@@H:6]([C:7]=3[CH:8]=[CH:9][CH:10]=2)[CH2:5][C@H:4]([NH:28][C:29](=[O:35])[N:30]([CH2:31][CH3:32])[CH2:33][CH3:34])[CH2:3][N:2]1[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 13559044HCID 13559044, compound

Product 1

HCID 86742052HCID 86742052, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

213 mg (0.45 mmol) of 3-[6-methyl-2-[3-(tetrahydropyran-2-yloxy)propynyl]-8α-ergolinyl]-1,1-diethylurea is heated under reflux in 10 ml of ethanol with 2 ml of water and 176 mg (0.7 mmol) of pyridinium p-toluenesulfonate under argon for one hour. After evaporation and distribution in ethyl acetate and saturated bicarbonate solution, the organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue is chromatographed over silica gel first with ethyl acetate/acetone=1:1 and later with methylene chloride/acetone=12:1. Recrystallization from ethyl acetate/hexane yields 90 mg (51%) of 3-[2-(1-hydroxypropyn-3-yl)-6-methyl-8α-ergolinyl]-1,1-diethylurea,

Workup

  1. customAfter evaporation and distribution in ethyl acetate
  2. washsaturated bicarbonate solution, the organic phase is washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed over silica gel first with ethyl acetate/acetone=1:1 and later with methylene chloride/acetone=12:1
  7. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1460d40db3a34a89ad563db249a486e2
Source dataset
uspto-grants-1989_07
Patent number
US04847262

Reaction notes

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