Acetic Acid → HCID 89526567, compound

HRID 1466168Notes

Reaction equation

HRID 1466168 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][C:12]1=[O:17])[CH2:5]2.CC(O)=O.[O:22]=[C:23]1[C:27]2[CH:28]=[CH:29][C:30]([CH2:32][CH:33]=O)=[CH:31][C:26]=2[CH2:25][O:24]1.[BH3-]C#N.[Na+]>C(Cl)Cl.CO.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([N:11]1[CH2:16][CH2:15][N:14]([CH2:33][CH2:32][C:30]3[CH:29]=[CH:28][C:27]4[C:23](=[O:22])[O:24][CH2:25][C:26]=4[CH:31]=3)[CH2:13][C:12]1=[O:17])[CH2:5]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehydeHCID 89526040HCID 89526040, compound

Product 1

HCID 89526567HCID 89526567, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of product from Step C (0.39 mmol) in 20 mL of DCM/MeOH (3/1, v/v) was added HOAc (47 mg, 0.78 mmol), (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (68 mg, 0.39 mmol) and NaBH3CN (49 mg, 0.78 mmol), and the mixture was stirred at RT for 2 hours. The reaction was diluted with DCM, washed with brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give the title product.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-585b9b0d4c7543cfbbf45ed4496fb4eb
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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