Acetic Acid → HCID 178441494, compound

HRID 2255549Notes

Reaction equation

HRID 2255549 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH2:16][CH2:17][CH2:18][CH3:19])[N:10]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:37][N:36]=[N:35][N:34]=3)=[CH:23][CH:22]=1)[C:9]2=[O:38])(=O)C.[OH-].[Na+].CCCCCC.C(O)(=O)C>CO>[CH2:16]([C:11]1[N:10]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:34][N:35]=[N:36][N:37]=3)=[CH:25][CH:26]=2)[C:9](=[O:38])[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH2:5][OH:4])[CH:7]=2)[N:12]=1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8058HexaneHCID 14798Sodium HydroxideHCID 178441495HCID 178441495, compound

Product 1

HCID 178441494HCID 178441494, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.2 g (0.38 mmol) of the product of Example 63 was dissolved in 5 mL of MeOH and was treated with 1 mL of 1N NaOH (1.0 mmol) and stirred over night. The resulting solution was extracted with EtOAc (3×10 mL). The organic phase was washed with water (2×5 mL) and brine (1×5 mL) and dried over MgSO4. The mixture was filtered and concentrated in vacuo and the residue was purified by flash chromatography over silica gel eluting with 80:19:1 EtOAc: hexane:acetic acid to give 0.17 g (0.36 mmol) of a white foam, 93% yield. 1H-NMR (CD3OD): 0.88 (t, 3H, J=7.38 Hz), 1.41 (m, 2H), 1.48 (m, 2H), 2.73 (3 line m, 2H, J=8.03 Hz), 4.60 (s, 2H), 5.38 (bs, 2H), 7.08 (m, 4 H), 7.20 (m, 1H), 7.50 (m, 2H), 7.61 (m, 2H), 7.77 (dd, 1H, J=2.0, 9.0 Hz), 8.17 (s, 1H). FABMS m/e: 467 (M+ +1) calc. for C27H26N6O2

Workup

  1. extractionThe resulting solution was extracted with EtOAc (3×10 mL)
  2. washThe organic phase was washed with water (2×5 mL) and brine (1×5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by flash chromatography over silica gel eluting with 80:19:1 EtOAc

Sources & evidence

ORD record
ord-cce4aa729ed84af18a0fff1f95660ccd
Source dataset
uspto-grants-1993_08
Patent number
US05240928

Reaction notes

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