HCID 22612367, compound → HCID 22612086, compound

HRID 844067Notes

Reaction equation

HRID 844067 reaction equation
[OH:1][C:2]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH:12][C:13](=[O:33])[C:14]2[CH:19]=[CH:18][CH:17]=[N:16][C:15]=2[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3([CH3:32])OCC[O:28]3)[CH:22]=2)[CH2:7][CH2:6]1)([CH3:4])[CH3:3]>C(O)(=O)C.C(OCC)(=O)C>[C:27]([C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[O:20][C:15]1[N:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]([NH:12][CH2:11][CH:8]1[CH2:7][CH2:6][CH:5]([C:2]([OH:1])([CH3:4])[CH3:3])[CH2:10][CH2:9]1)=[O:33])(=[O:28])[CH3:32]

Participants

4

Reactant 1

HCID 22612367HCID 22612367, compound

Product 1

HCID 22612086HCID 22612086, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[4-(1-Hydroxy-1-methyl-ethyl)-cyclohexylmethyl]-2-[3-(2-methyl-[1,3]dioxolan-2-yl)-phenoxy]-nicotinamide (0.400 grams, 0.88 mmole) in acetic acid (10 ml) was stirred for 3 hours at room temperature. The mixture was diluted with 250 ml ethyl acetate, washed with 1 N NaOH, water and brine, dried over MgSO4, filtered and concentrated to an oil which was purified by chromatography on silica eluting with 40% ethyl acetate/hexane. Recrystalization gave a solid. (0.055 g). M.P. 105-107° C.; Anal. calcd. for C24H30N2O4: C, 70.22; H, 7.37; N, 6.82. Found: C, 68.43; H, 7.32; N, 6.71.

Workup

  1. washwashed with 1 N NaOH, water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil which
  5. customwas purified by chromatography on silica eluting with 40% ethyl acetate/hexane
  6. customRecrystalization
  7. customgave a solid

Sources & evidence

ORD record
ord-3b5d83fd7f994649b5b80f7d80ab488b
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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