Water → HCID 70564858, compound

HRID 1477922Notes

Reaction equation

HRID 1477922 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:17]2[C:25]3[C:20](=[C:21]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)([CH2:15][CH3:16])[CH2:9][CH2:10][C:11](OC)=[O:12])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:17]2[C:25]3[C:20](=[C:21]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)([CH2:9][CH2:10][CH2:11][OH:12])[CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 70562931HCID 70562931, compound

Product 1

HCID 70564858HCID 70564858, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(4-chlorophenyl)-4-(4-(methylsulfonamido)-1H-indol-1-yl)hexanoate (20 mg, 0.045 mmol), as described in Example 44 Step E, in tetrahydrofuran (2 mL) was added lithium aluminium hydride (2.5 mg, 0.0675 mmol) at 0° C. The mixture was gradually warmed to room temperature and stirred for 4 h. Water (1 mL) was carefully added to the reaction mixture, and extracted with ethyl acetate. The combined organic layers were washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by PREP-TLC eluting with PE/EA (2/1, v/v) to give the title compound as colorless oil. LC/MS m/z=421.0[M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine (30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified
  7. washby PREP-TLC eluting with PE/EA (2/1

Sources & evidence

ORD record
ord-681469dbfd604b6b9dd45281a73d5a44
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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