Aluminium lithium hydride → HCID 68458113, compound

HRID 2358615Notes

Reaction equation

HRID 2358615 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([NH:18][C:19]2[C:28]3[C:23](=[N:24][C:25]([CH3:29])=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[CH:6]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:29][C:25]1[N:24]=[C:23]2[C:28]([C:19]([NH:18][C:7]3[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[CH:9][C:8]=3[S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:20][CH:21]=[N:22]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68460795HCID 68460795, compound

Product 1

HCID 68458113HCID 68458113, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 53c (2.30 g, 5.54 mmol) in 60 mL of THF was reacted with the LiAlH4 (420 mg, 11.0 mmol) for 18 h followed quenching with dilute HCl. Adjusted to pH 10 with NH4OH. Extracted with CH2Cl2, dried over MgSO4 filtered and concentrated under vacuum giving the crude title compound which was purified by HPLC with TFA providing the trifluoroacetic acid salt (325 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.76 (s, 3H) 3.99 (br. s, 1H) 4.58 (s, 2H) 6.31 (d, J=7.35 Hz, 1H) 7.25 (s, 5H) 7.40 (m, 2H) 7.46 (s, 1H) 7.78 (d, J=8.82 Hz, 1H) 8.42 (d, J=6.99 Hz, 1H) 8.95 (d, J=8.46 Hz, 1H) 11.06 (br. s., 1H) 14.44 (br. s., 1H); MS (ESI+) m/z 374 (M+H)+.

Workup

  1. customfollowed quenching with dilute HCl
  2. extractionExtracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-93dcbbef14f9432c9d0b6b370f00615d
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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