Water → HCID 52951616, compound

HRID 508607Notes

Reaction equation

HRID 508607 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[N:8]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[CH3:27][S:24]([C:21]1[CH:20]=[CH:19][C:18]([N:9]2[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:11][C:7]([CH2:6][CH2:5][CH2:4][OH:3])=[N:8]2)=[CH:23][CH:22]=1)(=[O:25])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 52951277HCID 52951277, compound

Product 1

HCID 52951616HCID 52951616, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ester 17 (1.27 g, 4 mmol) in 40 mL of THF was added LiAlH4 (0.24 mg, 6.4 mmol). The reaction mixture was stirred for 6 hours at room temperature. EtOAC (5 mL) and water (10 mL) were added successively. The solvent was removed in vacuo and the resulting solid was filtered. The crude product was purified by column chromatography (EtOAc/Hexanes=7:3) to give the titled compound (0.97 g, 85%) as a white solid mp 119.5-123.4° C. 1H NMR (300 MHz, DMSO-d6): δ 7.91 (d, J=9 Hz, 2H), 7.46 (d, J=9 Hz, 2H), 7.43-7.37 (m, 3H), 7.31-7.25 (m, 2H), 6.56 (s, 1H), 4.52 (t, J=5 Hz, 1H), 3.54-3.46 (m, 2H), 3.24 (s, 3H), 2.79-2.60 (m, 2H), 1.88-1.77 (m, 2H).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationthe resulting solid was filtered
  3. customThe crude product was purified by column chromatography (EtOAc/Hexanes=7:3)

Sources & evidence

ORD record
ord-f0a53c69d5b943c2bef31017f868041c
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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