Sodium Hydroxide → HCID 86615562, compound

HRID 605318Notes

Reaction equation

HRID 605318 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([CH2:27][CH2:28][CH:29]([CH:31]4[C:47]5([CH3:48])[CH:34]([CH:35]6[CH:44]([CH2:45][CH:46]5[O:49]C=O)[C:43]5([CH3:52])[CH:38]([CH2:39][CH:40]([O:53]C=O)[CH2:41][CH2:42]5)[CH2:37][CH:36]6[O:56]C=O)[CH2:33][CH2:32]4)[CH3:30])=[O:26])=[CH:20][CH:19]=3)=[C:13]([NH:59][C:60]3[C:61]4[CH:69]=[CH:68][C:67]([CH:70]([CH3:72])[CH3:71])=[N:66][C:62]=4[N:63]=[CH:64][N:65]=3)[CH:12]=2)=[O:10])=[N:6][CH:7]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:10])[C:11]2[CH:16]=[CH:15][C:14]([S:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:26])[CH2:27][CH2:28][CH:29]([CH:31]4[C:47]5([CH3:48])[CH:34]([CH:35]6[CH:44]([CH2:45][CH:46]5[OH:49])[C:43]5([CH3:52])[CH:38]([CH2:39][CH:40]([OH:53])[CH2:41][CH2:42]5)[CH2:37][CH:36]6[OH:56])[CH2:33][CH2:32]4)[CH3:30])=[CH:20][CH:19]=3)=[C:13]([NH:59][C:60]3[C:61]4[CH:69]=[CH:68][C:67]([CH:70]([CH3:72])[CH3:71])=[N:66][C:62]=4[N:63]=[CH:64][N:65]=3)[CH:12]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86615563HCID 86615563, compound

Product 1

HCID 86615562HCID 86615562, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product of Example 358B (162 mg, 0.1527 mmol) was suspended in methanol (2 mL) and treated with 10% sodium hydroxide in methanol (2 mL), sonicated briefly to achieve dissolution, and stirred at room temperature for one hour. The solvent was removed by rotary evaporation in vacuo and the residue taken up in ethyl acetate (150 mL) and water (50 mL). The aqueous pH was adjusted to 5 with 1N aqueous hydrochloric acid and the layers separated. The organic phase was washed with water (50 mL) and brine (50 mL), then dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation. Purification by silica gel flash chromatography with a gradient of 8% to 10% methanol/methylene chloride afforded the title compound (137 mg, 0.140 mmol, 92%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 0.60 (s, 3 H) 0.81 (s, 3 H) 0.98 (d, J=5.88 Hz, 3 H) 1.12-2.52 (m, 24 H) 1.33 (d, J=6.99 Hz, 6 H) 3.12-3.31 (m, 2 H) 3.55-3.69 (m, 1 H) 3.75-3.87 (m, 1 H) 4.02 (d, J=3.31 Hz, 1 H) 4.13 (d, J=3.68 Hz, 1 H) 4.32 (d, J=4.41 Hz, 1 H) 6.89-7.05 (m, 1 H) 7.40 (d, J=8.46 Hz, 2 H) 7.57-7.66 (m, 1 H) 7.68 (d, J=8.46 Hz, 2 H) 7.81-7.95 (m, 1 H) 8.01-8.12 (m, 2 H) 8.16 (d, J=8.82 Hz, 1 H) 8.50 (d, J=2.57 Hz, 1 H) 8.53-8.67 (m, 1 H) 8.76-8.96 (m, 1 H) 10.09 (s, 1 H) 10.21 (br s, 1 H) 10.97 (br s, 1 H); MS (ESI+) m/z 977/979 (M+H)+.

Workup

  1. customsonicated briefly
  2. dissolutiondissolution
  3. customThe solvent was removed by rotary evaporation in vacuo
  4. customthe layers separated
  5. washThe organic phase was washed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customPurification by silica gel flash chromatography with a gradient of 8% to 10% methanol/methylene chloride

Sources & evidence

ORD record
ord-6c6e882b18574e66bcc28e1e828603d6
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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