1,1-Dichloroethane → HCID 59204268, compound

HRID 2242248Notes

Reaction equation

HRID 2242248 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[N:17]=[CH:18][C:19]([CH:22]=O)=[N:20][CH:21]=3)[N:12]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH2:24]([O:26][C:27]([C@H:29]1[CH2:32][C@@H:31]([NH2:33])[CH2:30]1)=[O:28])[CH3:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClC(Cl)C>>[CH2:24]([O:26][C:27]([CH:29]1[CH2:32][CH:31]([NH:33][CH2:22][C:19]2[CH:18]=[N:17][C:16]([C:13]3[N:12]=[C:11]([C:8]4[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=4)[O:15][N:14]=3)=[CH:21][N:20]=2)[CH2:30]1)=[O:28])[CH3:25]

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 59204300HCID 59204300, compoundHCID 178472513HCID 178472513, compound

Product 1

HCID 59204268HCID 59204268, compound

Procedure

A solution of 5-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyrazine-2-carbaldehyde (0.100 g, 0.32 mmol), cis-3-amino-cyclobutanecarboxylic acid ethyl ester (0.056 g, 0.388 mmol), sodium triacetoxyborohydride (0.082 g, 0.388 mmol) and dichloroethane (5.0 mL) was stirred at room temperature for 12 hours. The reaction mixture was quenched with 1N NaOH (10 mL) and the organic layer was isolated, washed with H2O (2×10 mL) and brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo to yield the title compound as a crude solid.

Workup

  1. customThe reaction mixture was quenched with 1N NaOH (10 mL)
  2. customthe organic layer was isolated
  3. washwashed with H2O (2×10 mL) and brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7027a3927b15445ab5c6d2af42497341
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

Loading…