Diisobutylaluminumhydride → HCID 57378403, compound

HRID 218210Notes

Reaction equation

HRID 218210 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13](=O)[C:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23](=[O:42])(=[O:41])[NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[N:32]2[C:40]3[C:35](=[N:36][CH:37]=[CH:38][CH:39]=3)[N:34]=[N:33]2)=[CH:19][CH:18]=1)([CH3:16])[CH3:15]>C(Cl)Cl>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([NH:24][S:23]([C:20]2[CH:21]=[CH:22][C:17]([C:14]([CH3:15])([CH3:16])[CH2:13][OH:12])=[CH:18][CH:19]=2)(=[O:42])=[O:41])=[C:26]([N:32]2[C:40]3[C:35](=[N:36][CH:37]=[CH:38][CH:39]=3)[N:34]=[N:33]2)[CH:27]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 59428125HCID 59428125, compound

Product 1

HCID 57378403HCID 57378403, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIBAL-H (diisobutylaluminum hydride)(0.71 mL, 1.0 M solution in CH2Cl2) was added to 2-[4-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenylsulfamoyl)-phenyl]-2-methyl-propionic acid methyl ester (synthesized according to general procedures F and G, 137 mg, 0.282 mmol) in CH2Cl2 (3 mL) at −78° C. After 1 hour, LCMS indicated a 2:1 ratio of the desired product and corresponding aldehyde intermediate. 1 N HCl (2 mL) was added to the reaction mixture, the flask was warmed to room temperature, and the solution was diluted with EtOAc (30 mL). The EtOAc layer was separated, dried (Na2SO4), and evaporated in vacuo. The resultant crude residue was treated with NaBH4 (30 mg, excess) in MeOH (3 mL) at room temperature for 10 minutes and directly purified by preparative HPLC to afford the title compound as a white powder: MS (ES) M+H expected 458.1, found 458.0.

Sources & evidence

ORD record
ord-14d7fe45a2bf41b1886fa7c3ab74b3a3
Source dataset
uspto-grants-2012_06
Patent number
US08198309B2

Reaction notes

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