Chloroform methanol → Levcromakalim

HRID 235675Notes

Reaction equation

HRID 235675 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]2[O:7][C:8]([CH3:19])([CH3:18])[C@@H:9]([OH:17])[C@H:10]([N:11]3[CH2:15][CH2:14][CH2:13][CH:12]3[OH:16])[C:5]=2[CH:4]=1)#[N:2].I([O-])(=O)(=O)=O.[Na+].C(Cl)(Cl)Cl.CO.CCCCCCC.C(OCC)(=O)C.C(N(CC)CC)C>O.CO>[C:1]([C:3]1[CH:21]=[CH:20][C:6]2[O:7][C:8]([CH3:19])([CH3:18])[C@@H:9]([OH:17])[C@H:10]([N:11]3[CH2:15][CH2:14][CH2:13][C:12]3=[O:16])[C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 21584188Chloroform methanolHCID 22311133HCID 22311133, compoundHCID 23667635Sodium periodateHCID 67881644HCID 67881644, compound

Product 1

HCID 93504Levcromakalim

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

6-Cyano-3,4-dihyro-2,2-dimethyl-trans-4-(2-hydroxy-1-pyrrolidinyl)-2H-benzo[b]pyran-3-ol (5 mg), dissolved in methanol water (1 ml) was treated with an excess of sodium periodate with stirring during 15 hours at room temperature. Evaporation of solvents and extraction by ethyl acetate gave material having identical thin layer characteristics when applied to silica gel plates developed in either chloroform-methanol (15:1) or heptane-ethyl acetate-triethylamine and infra red spectrum to the title compound reported in Example 1 of U.S. Pat. No. 4,446,113.

Workup

  1. customEvaporation of solvents and extraction by ethyl acetate
  2. customgave material

Sources & evidence

ORD record
ord-13ee768044bc4073ace3e7dc76a2bd3e
Source dataset
uspto-grants-1987_02
Patent number
US04640928

Reaction notes

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