Diethyl Ether → HCID 71543440, compound

HRID 1746417Notes

Reaction equation

HRID 1746417 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([C:23]3[CH:33]=[CH:32][C:26]([C:27](OCC)=[O:28])=[CH:25][C:24]=3[CH3:34])[CH2:19][CH:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:35])[O:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)C>C1COCC1.ClCCl.CO>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([C:23]3[CH:33]=[CH:32][C:26]([CH2:27][OH:28])=[CH:25][C:24]=3[CH3:34])[CH2:19][CH:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:35])[O:4][N:3]=1

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 86731592HCID 86731592, compound

Product 1

HCID 71543440HCID 71543440, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 4-(4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutylphenylsulfonamido)-3-methylbenzoate (40 mg, 0.080 mmol) in THF (5 mL) stirred under nitrogen at 0° C. was added a solution of LiAlH4 1M in diethyl ether (0.160 mL, 0.160 mmol) dropwise. The reaction mixture was stirred at 0° C. for 30 minutes. The reaction was then allowed to warm up to room temperature and stirred for 2 hours. The reaction mixture was diluted with dichloromethane (10 mL). The organic phase was washed with water 10 mL, and saturated brine 10 mL, dried using a hydrophobic frit and concentrated under a stream of nitrogen in the Radleys blowdown apparatus to give the crude product. The crude was dissolved in 1:1 MeOH:DMSO 1 mL and purified by mass directed autoprep on a Sunfire C18 column using acetonitrile:water with a formic acid modifier. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the required product, 23.6 mg colorless oil which solidified. LCMS (M+1) 459, RT 1.14 mins.

Workup

  1. temperatureto warm up to room temperature
  2. stirringstirred for 2 hours
  3. washThe organic phase was washed with water 10 mL, and saturated brine 10 mL
  4. customdried
  5. concentrationconcentrated under a stream of nitrogen in the Radleys blowdown apparatus
  6. customto give the crude product
  7. customDMSO 1 mL and purified by mass
  8. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-3f23f0ca9a0f4738a5d2800b22028bb1
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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