Aluminium lithium hydride → HCID 67163383, compound

HRID 553099Notes

Reaction equation

HRID 553099 reaction equation
C[O:2][C:3](=O)[C:4]([N:7]1[CH:11]=[C:10]([NH:12][C:13](=[O:26])[CH:14]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:16][CH3:17])[N:9]=[CH:8]1)([CH3:6])[CH3:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[C:22]([O:21][C:19](=[O:20])[NH:18][CH:14]([C:13](=[O:26])[NH:12][C:10]1[N:9]=[CH:8][N:7]([C:4]([CH3:6])([CH3:5])[CH2:3][OH:2])[CH:11]=1)[CH2:15][CH2:16][CH3:17])([CH3:23])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67163051HCID 67163051, compound

Product 1

HCID 67163383HCID 67163383, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[4-(2-tert-Butoxycarbonylamino-pentanoylamino)-imidazol-1-yl]-2-methyl-propionic acid methyl ester (9.6 g, 25.2 mmol) in 100 mL of diethyl ether at 0° C. is added 1.0 M lithium aluminum hydride (37.9 mL, 37.9 mmol) in diethylether dropwise over 1 h. The reaction is stirred at 0° C. for 15 min and warmed to rt for 1 h. The reaction is slowly quenched with 200 mL of water and ethyl acetate (200 mL). The reaction is filtered and the aqueous is extracted with ethylacetate, dried, and concentrated. The resultant residue is purified by silica gel chromatography to provide the title compound (5.8 g); MS m/z 355.3 (M+1).

Workup

  1. temperaturewarmed to rt for 1 h
  2. customThe reaction is slowly quenched with 200 mL of water and ethyl acetate (200 mL)
  3. filtrationThe reaction is filtered
  4. extractionthe aqueous is extracted with ethylacetate
  5. customdried
  6. concentrationconcentrated
  7. customThe resultant residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-1ed23f5e5cc84b11b1cc31512a8e6c79
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

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