Ethyl Acetate → HCID 89618522, compound

HRID 926717Notes

Reaction equation

HRID 926717 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[C@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20]1[CH:25]=[CH:24][N:23]2[N:26]=[CH:27][C:28]([C:29]([NH:31][CH2:32][C@@H:33]([OH:39])[CH2:34][C:35](OC)=[O:36])=[O:30])=[C:22]2[CH:21]=1.CCOC(C)=O.[NH4+].[Cl-]>C1COCC1.O>[F:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[C@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20]1[CH:25]=[CH:24][N:23]2[N:26]=[CH:27][C:28]([C:29]([NH:31][CH2:32][C@@H:33]([OH:39])[CH2:34][CH2:35][OH:36])=[O:30])=[C:22]2[CH:21]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 89618899HCID 89618899, compound

Product 1

HCID 89618522HCID 89618522, compoundYield 10.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LAH (12 mg, 0.33 mmol) was added portionwise to a solution of (S)-methyl 4-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxamido)-3-hydroxybutanoate (100 mg, 0.22 mmol) in THF (2 mL) at 0-5° C. and continued stirring at the same temperature for 1 h. EtOAc was added to the above reaction mixture followed by NH4Cl solution and water. Organic layer separated was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude product, which was purified by Preparative TLC (using Silicagel GF254, 1000 u coated 20×20 cm dimension glass plate and 7% MeOH in CHCl3 as eluent) to afford 10.3 mg of the title compound.

Workup

  1. customOrganic layer separated
  2. dry with materialwas dried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product, which
  5. customwas purified by Preparative TLC (using Silicagel GF254, 1000 u coated 20×20 cm dimension glass plate and 7% MeOH in CHCl3 as eluent)

Sources & evidence

ORD record
ord-4503ffc936644cc48bbc09c20670bc18
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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