Acetic Acid → HCID 135896314, compound

HRID 2110617Notes

Reaction equation

HRID 2110617 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[NH2:8][C@@:9]1([CH2:38][CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[C:18]2C(=[CH:14][CH:15]=[CH:16][CH:17]=2)C(O)=[C:11]([C:20]2[NH:25][C:24]3[CH:26]=[CH:27][C:28]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][C:23]=3[S:22](=[O:36])(=[O:35])[N:21]=2)[C:10]1=[O:37].C(N(CC)C(C)C)(C)C.[CH3:53][C:54]1[CH:61]=[CH:60][CH:59]=[C:58]([CH3:62])[C:55]=1[CH:56]=O.[O-]S([O-])(=O)=O.[Mg+2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C.C(Cl)Cl>[CH3:53][C:54]1[CH:61]=[CH:60][CH:59]=[C:58]([CH3:62])[C:55]=1[CH2:56][NH:8][C@@:9]1([CH2:38][CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[C:18]2[C:2](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:3]([OH:5])=[C:11]([C:20]2[NH:25][C:24]3[CH:26]=[CH:27][C:28]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][C:23]=3[S:22](=[O:36])(=[O:35])[N:21]=2)[C:10]1=[O:37]

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 81531DiisopropylethylamineHCID 5838412,6-DimethylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 135885139HCID 135885139, compound

Product 1

HCID 135896314HCID 135896314, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of the product of Example 119 (0.4 g, 0.62 mmol) in dichloroethane (6 mL) was added N,N-diisopropylethylamine (0.22 mL, 1.23 mmol). The mixture was stirred at room temperature until homogenous before 2,6-dimethylbenzaldehyde (0.17 g, 1.23 mmol) and MgSO4 (0.15 g) were added. The reaction mixture was heated at 50° C. for 18 h, cooled to room temperature and filtered. To the filtrate was added sodium triacetoxyborohydride (0.21 g, 0.99 mmol) and glacial acetic acid (0.11 mL, 1.86 mmol), and the resulting mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with CH2Cl2 (25 mL) and washed with distilled H2O (2×10 mL), dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (1% to 3% MeOH/CH2Cl2 gradient) afforded the title compound as a light orange solid (0.22 g, 40%). 1H NMR (300 MHz, DMSO-D6) δ ppm 13.96 (s, 1H), 9.98 (s, 1H), 8.23 (d, J=7.72 Hz, 1H), 8.03 (d, J=7.72 Hz, 1H), 7.70-7.79 (m, 1H), 7.64 (t, J=7.35 Hz, 1H), 7.45-7.55 (m, 2H), 7.32-7.42 (m, 1H), 7.14-7.22 (m, 1H), 7.04-7.10 (m, 2H), 3.64-3.79 (m, 1H), 3.38-3.43 (m, 1H), 3.02 (s, 3H), 2.31-2.43 (m, 1H), 2.27 (s, 6H), 1.99-2.12 (m, 1H), 0.94-1.12 (m, 1H), 0.68 (s, 9H), 0.32-0.48 (m, 1H); MS m/z 651.3 (M+H)+.

Workup

  1. additionwere added
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. washwashed with distilled H2O (2×10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d935d17501334bcf86cefd0cd61b7570
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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