HCID 11692407, compound → HCID 68514413, compound

HRID 748939Notes

Reaction equation

HRID 748939 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[C:12]=2[C:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:27][CH:26]=2)=[O:24])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[C:12]=2[CH:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:27][CH:26]=2)[OH:24])=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 11692407HCID 11692407, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 68514413HCID 68514413, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve the compound of Example 74 (200 mg, 0.37 mmol) in THF (30 mL). Add lithium aluminum hydride (LAH, 70.3 mg). Quench with ice and water. Acidify with 1M aqueous HCl and make the solution slightly basic with aqueous NaHCO3. Extract with 25% i-PrOH in CHCl3. Purify the crude product using an SCX column eluting with 2M NH3/MeOH to afford 185 mg of the title compound (92%) LCMS: m/z=546 (M+H)+

Workup

  1. customQuench with ice and water
  2. extractionExtract with 25% i-PrOH in CHCl3
  3. customPurify the crude product
  4. washeluting with 2M NH3/MeOH

Sources & evidence

ORD record
ord-c0a46515ba8747ce87e5513faebfd27d
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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