Acetic Acid → HCID 89662755, compound

HRID 1479085Notes

Reaction equation

HRID 1479085 reaction equation
Cl.[Cl:2][C:3]1[C:11]([CH3:12])=[N:10][C:9]2[N:5]([N:6]=[C:7]3[C:15]([CH3:17])([CH3:16])[N:14]([C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)=[O:19])[CH2:13][C:8]3=2)[C:4]=1[CH3:33].[CH3:34][C:35]([CH3:37])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O.[OH-].[Na+]>ClCCCl>[Cl:2][C:3]1[C:11]([CH3:12])=[N:10][C:9]2[N:5]([N:6]=[C:7]3[C:15]([CH3:16])([CH3:17])[N:14]([C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH:27]4[CH2:28][CH2:29][N:30]([CH:35]([CH3:37])[CH3:34])[CH2:31][CH2:32]4)=[O:19])[CH2:13][C:8]3=2)[C:4]=1[CH3:33]

Participants

7

Reactant 5

HCID 176Acetic Acid2×HCID 180Acetone2×HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydride2×HCID 122429360HCID 122429360, compound

Product 1

HCID 89662755HCID 89662755, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of Example 100 (98 mg; 0.22 mmol; 1 eq.), acetone (95 μL; 1.3 mmol; 6 eq.), sodium triacetoxyborohydride (183 mg; 0.86 mmol; 4 eq.) and AcOH (15 μL; 0.26 mmol; 1 eq.) in DCE (5 mL) was stirred at room temperature for 16 hours. Acetone (95 μL; 1.3 mmol; 6 eq.), sodium triacetoxyborohydride (183 mg; 0.86 mmol; 4 eq.) and AcOH (15 μL; 0.26 mmol; 1 eq.) were added and the resulting mixture was stirred at room temperature for 24 hours. 1M NaOH was added and the two phases separated. The aqueous layer was extracted with DCM (2×). The combined organic phase was dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (5% to 20% MeOH in DCM) afforded the title compound (78 mg, 72%) as a colourless oil. 1H NMR (DMSO-d6) δ 7.44-7.33 (m, 1H), 7.24 (dd, J=7.4, 1.7 Hz, 1H), 7.18-7.09 (m, 1H), 7.00 (t, J=7.4 Hz, 1H), 4.61-4.42 (m, 2H), 4.42-4.27 (m, 1H), 2.83 (s, 3H), 2.63-2.52 (m, 4H), 2.36-2.21 (m, 2H), 1.98-1.74 (m, 8H), 1.68-1.44 (m, 2H), 0.79 (d, J=6.2 Hz, 6H). HPLC (max plot) 86.3%, Rt 3.27 min. UPLC/MS: (MS+) 496.5 ([M+H]+).

Workup

  1. customthe two phases separated
  2. extractionThe aqueous layer was extracted with DCM (2×)
  3. dry with materialThe combined organic phase was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (5% to 20% MeOH in DCM)

Sources & evidence

ORD record
ord-154a9b30471044ffa40ac96a85c24de5
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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