1,4-Dioxane → HCID 25100740, compound

HRID 1013281Notes

Reaction equation

HRID 1013281 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:30])=[C:16]2[C:31]([O:33]CC)=[O:32])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O1CCOCC1>[Li+].[OH-]>[CH3:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:15]([CH2:14][CH2:13][CH2:12][O:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:16]=1[C:31]([OH:33])=[O:32]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 67316147HCID 67316147, compound

Product 1

HCID 25100740HCID 25100740, compound

Reagents, catalysts & solvents 1

HCID 3939Lithium HydroxideSolvent

Procedure

A mixture of EXAMPLE 31D in 1N LiOH:dioxane (0.5 mL: 2 mL) was heated under microwave conditions (CEM Discover) at 130° C. for 30 minutes. The mixture was quenched with 1NHCl aqueous mixture (0.5 mL) and extracted with ethyl acetate. The extract was dried (Na2SO4), filtered, and concentrated. The concentrate was purified by reverse phase HPLC (Zorbax SB-C18, 20-100% acetonitrile/water/0.1% trifluoroacetic acid). 1H NMR (400 MHz, DMSO-d6) δ 12.73 (bs, 1H), 8.23 (d, 1H), 7.87 (d, 1H), 7.66 (d, 1H), 7.52 (m, 3H), 7.38 (t, 1H), 7.26 (m, 4H), 7.12 (m, 2H), 7.04 (m, 1H), 6.87 (d, 2H), 4.91 (t, 2H), 4.19 (t, 2H), 2.38 (m, 2H), 2.01 (s, 3H).

Workup

  1. customThe mixture was quenched with 1NHCl aqueous mixture (0.5 mL)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by reverse phase HPLC (Zorbax SB-C18, 20-100% acetonitrile/water/0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-46def3a8c59a47b1bff4d577b383a0c0
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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