HCID 22660757, compound → HCID 25234700, compound

HRID 508371Notes

Reaction equation

HRID 508371 reaction equation
[C:1]([C:5]1[C:6]([O:35][CH3:36])=[C:7]([CH:24]=[C:25]([N:27]2[CH:32]=[CH:31][C:30](=[O:33])[NH:29][C:28]2=[O:34])[CH:26]=1)/[CH:8]=[CH:9]/[C:10]1[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][C:11]=1[C:12](Cl)=[O:13])([CH3:4])([CH3:3])[CH3:2].[H-].C(O[Al+2])(C)(C)C.[Li+].[H-].[H-]>C1COCC1>[C:1]([C:5]1[C:6]([O:35][CH3:36])=[C:7]([CH:24]=[C:25]([N:27]2[CH:32]=[CH:31][C:30](=[O:33])[NH:29][C:28]2=[O:34])[CH:26]=1)/[CH:8]=[CH:9]/[C:10]1[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:21])=[O:22])=[CH:15][C:11]=1[CH2:12][OH:13])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 22660757HCID 22660757, compoundHCID 86652125HCID 86652125, compound

Product 1

HCID 25234700HCID 25234700, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the product from Example 126, Part A (375 mg, 0.705 mmol) in anhydrous THF (5 ml) at 0° C. under N2 gas was added a 1.0 M solution of lithium tert-butoxyaluminiumhydride (1.8 ml, 1.8 mmol) dropwise. The resulting mixture was stirred at 0° C. for 30 min, and then allowed to warm to room temperature and was stirred for 1 h. The mixture was partitioned between 1 N aq. HCl (10 ml) and EtOAc (2×10 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 3% MeOH in CH2Cl2 as the eluent to give the title compound (220 mg, 63%). 1H NMR (300 MHz, DMSO-d6) δ ppm 11.41 (s, 1H) 9.82 (s, 1H) 7.73 (t, J=8.27 Hz, 2H) 7.66 (d, J=2.57 Hz, 1H) 7.31-7.39 (m, 2H) 7.20 (d, J=2.57 Hz, 1H) 7.12-7.19 (m, 2H) 5.65 (d, J=8.09 Hz, 1H) 5.28 (t, J=5.52 Hz, 1H) 4.65 (d, J=5.52 Hz, 2H) 3.79 (s, 3H) 3.00 (s, 3H) 1.38 (s, 9H).

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred for 1 h
  3. customThe mixture was partitioned between 1 N aq. HCl (10 ml) and EtOAc (2×10 ml)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel using 3% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-8babce2de0644bc88384927949f059dc
Source dataset
uspto-grants-2015_08
Patent number
US09095590B2

Reaction notes

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