Water → HCID 89954857, compound

HRID 705373Notes

Reaction equation

HRID 705373 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:27]=[C:26]([N:28]([CH2:33][C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=4)[S:29]([CH3:32])(=[O:31])=[O:30])[C:25]([CH:42]4[CH2:44][CH2:43]4)=[CH:24][C:18]=3[C:19]=2[C:20](OC)=[O:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][C:17]3[CH:27]=[C:26]([N:28]([CH2:33][C:34]4[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=4)[S:29]([CH3:32])(=[O:31])=[O:30])[C:25]([CH:42]4[CH2:43][CH2:44]4)=[CH:24][C:18]=3[C:19]=2[CH2:20][OH:21])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 89955656HCID 89955656, compound

Product 1

HCID 89954857HCID 89954857, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 18H (4.34 g, 7.09 mmol) in tetrahydrofuran (20 mL) at 5° C. under nitrogen was treated dropwise with a solution of 1 M lithium aluminum hydride (7.1 mL, 7.1 mmol). The reaction mixture was stirred for two hours at ambient temperature, and treated sequentially and dropwise with water (0.29 mL), 15% aqueous sodium hydroxide (0.29 mL) and water (0.875 mL). The resulting slurry was stirred for 20 minutes, diluted with ethyl acetate and filtered through diatomaceous earth. The diatomaceous earth was rinsed with ethyl acetate, and the combined filtrate was concentrated to an oil. The oil was diluted with dichloromethane and hexane and concentrated once again to give the title compound as a yellow foam (4.08 g, 99%). MS (ESI+) m/z 601 (M+NH4)+.

Workup

  1. stirringThe resulting slurry was stirred for 20 minutes
  2. filtrationfiltered through diatomaceous earth
  3. washThe diatomaceous earth was rinsed with ethyl acetate
  4. concentrationthe combined filtrate was concentrated to an oil
  5. additionThe oil was diluted with dichloromethane and hexane
  6. concentrationconcentrated once again

Sources & evidence

ORD record
ord-84edfd7c170f44f5b5d712453776f285
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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