Diisobutylaluminumhydride → HCID 57378403, compound

HRID 1480917Notes

Reaction equation

HRID 1480917 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 (diisobutylaluminium 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-bcbeda003ef24054b02c02d6b84cc4de
Source dataset
uspto-grants-2016_08
Patent number
US09409909B2

Reaction notes

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