Diisobutylaluminumhydride → HCID 178441826, compound

HRID 973668Notes

Reaction equation

HRID 973668 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:7]([C:15]([OH:17])=[O:16])=[C:8]([N:10](C)[C:11](=O)C)[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:7]([C:15]([OH:17])=[O:16])=[C:8]([NH:10][CH3:11])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 178441825HCID 178441825, compound

Product 1

HCID 178441826HCID 178441826, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound can be prepared from 2-butyl-4-(N-methylacetamido)-1-(2'-(tetrazol-5-yl)-biphen-4-yl)methylimidazole-5-carboxylic acid by reaction with 3 molar equivalents of diisobutyl-aluminum hydride in THF at room temperature followed by aqueous workup (extraction from 0.1% aqueous HOAc with EtOAc and isolation (SiO2, 35:65:1 CH2Cl2 /MeOH/ NH4OH). Alternatively' the title compound could be prepared from 4-methylamino-5-benzyloxycarbonyl-2-butyl-1-(2'-(N-triphenylmethyltetrazol-5-yl-biphen-4-yl)methylimidazole (mentioned in Example 18, Step 2) by reaction as outlined in Example 18, Step 3.

Sources & evidence

ORD record
ord-579d5252ecf6481ea0da221c68ccfadb
Source dataset
uspto-grants-1991_11
Patent number
US05064825

Reaction notes

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