Acetic Acid → HCID 178472516, compound

HRID 2242253Notes

Reaction equation

HRID 2242253 reaction equation
Cl.[CH2:2]([O:4][C:5]([C@H:7]1[CH2:10][C@@H:9]([NH2:11])[CH2:8]1)=[O:6])[CH3:3].[CH2:12]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]=[C:25]([C:27]3[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=3)[O:24][N:23]=2)=[CH:18][CH:17]=1)[CH:13]([CH3:15])[CH3:14].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH2:12]([C:16]1[CH:17]=[CH:18][C:19]([C:22]2[N:26]=[C:25]([C:27]3[CH:28]=[CH:29][C:30]([CH2:31][NH:11][C@@H:9]4[CH2:10][C@H:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH2:8]4)=[CH:33][CH:34]=3)[O:24][N:23]=2)=[CH:20][CH:21]=1)[CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 592043124-[3-(4-Isobutylphenyl)-1,2,4-oxadiazol-5-yl]benzaldehydeHCID 178472514HCID 178472514, compound

Product 1

HCID 178472516HCID 178472516, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

cis-3-Amino-cyclobutanecarboxylic acid ethyl ester hydrochloride (0.193 g, 1.35 mmol) was added to a solution of 4-[3-(4-isobutylphenyl)-1,2,4-oxadiazol-5-yl]benzaldehyde (0.333 g, 1.08 mmol), acetic acid (2 mL) and THF (18 mL) and stirred for 30 minutes. Sodium triacetoxyborohydride (0.500 g, 2.36 mmol) was added to the reaction mixture, stirred at room temperature for 16 hours, and concentrated in vacuo to give a white solid. The solid was triturated with water, filtered and dried to give the title compound (0.260 g, 55% yield) as a white solid.

Workup

  1. stirringstirred at room temperature for 16 hours
  2. concentrationconcentrated in vacuo
  3. customto give a white solid
  4. customThe solid was triturated with water
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-21e9c495d4164c65a9ae08cfbea54bd5
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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