Acetic Acid → HCID 68212638, compound

HRID 2202157Notes

Reaction equation

HRID 2202157 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[N:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:9]=2)=[CH:4][CH:3]=1.[CH3:25][C:26]([CH3:28])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C(O)(=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH:26]([CH3:28])[CH3:25])[CH2:15][CH2:14]3)[N:10]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 2724942TriacetoxyborohydrideHCID 67470977HCID 67470977, compound

Product 1

HCID 68212638HCID 68212638, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of INTERMEDIATE 5 (30 mg, 0.089 mmol) in DCM (0.5 mL) were added acetone (0.026 mL, 0.355 mmol), triacetoxyborohydride (75 mg, 0.355 mmol) and acetic acid (10.7 mg, 0.178 mmol). The mixture was stirred at room temperature overnight, quenched with 1 N NaOH, and extracted with EtOAc. The organic layer was washed with water, dried (MgSO4) and concentrated. The residue was purified by preparative TLC (4% MeOH/DCM) to give the title compound. LC-MS m/z 380.16 [M+H]+.

Workup

  1. customquenched with 1 N NaOH
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (4% MeOH/DCM)

Sources & evidence

ORD record
ord-ab455b3e6c37494cad5ea50f62e1e607
Source dataset
uspto-grants-2016_06
Patent number
US09365539B2

Reaction notes

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