Acetaldehyde → HCID 59841056, compound

HRID 1625136Notes

Reaction equation

HRID 1625136 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][CH:8]([C:13]1[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:21](=[O:29])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[CH3:30])[N:14]=1)[CH2:9][CH2:10][CH2:11][NH2:12])([CH3:4])([CH3:3])[CH3:2].[CH:32](=O)[CH3:33].[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:36].[Na+]>ClCCCl>[C:1]([O:5][C:6](=[O:31])[NH:7][CH:8]([C:13]1[N:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:21](=[O:29])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[CH3:30])[N:14]=1)[CH2:9][CH2:10][CH2:11][N:12]([CH2:32][CH3:33])[CH2:35][CH3:36])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59841070HCID 59841070, compound

Product 1

HCID 59841056HCID 59841056, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A 10-mL, one-neck, round bottomed flask equipped with a magnetic stirrer was purged with nitrogen; and then charged with the compound 104 (100 mg, 0.24 mmol) and 1,2-dichloroethane (2 mL). Acetaldehyde (42 mg, 0.85 mmol) and sodium triacetoxyborohydride (400 mg, 1.90 mmol) were subsequently added. The reaction mixture was stirred for 18 h at ambient temperature, evaporated to dryness, and the resulting residue was dissolved in methanol (20 mL). This methanolic solution was treated with 10% palladium on carbon (5 mg, 50% wet), stirred for 30 min, evaporated to dryness, and partitioned between 10% aqueous potassium carbonate (20 mL) and methylene chloride (20 mL). The organic layer was separated and dried over sodium sulfate. Filtration of the organic layer followed by concentration gave the compound 105 as a yellow oil, which was used without any further purification. 1H NMR (CDCl3) δ 7.51-7.63 (m, 5H), 7.41 (d, 1H, J=7.4 Hz), 7.29 (d, 1H, J=7.15 Hz), 7.22 (d, 1H, J=7.1 Hz), 6.10 (d, 1H, J=8.8 Hz), 4.38-4.52 (m, 1H), 2.81 (s, 3H), 2.32-2.50 (m, 4H), 2.08-2.27 (m, 2H), 1.47-1.73 (m, 4H), 1.42 (s, 9H, 1.25-1.38 (m, 1H), 0.96 (t, 6H, J=7.2 Hz); ESI-MS m/z=479 (MH+).

Workup

  1. customA 10-mL, one-neck, round bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. customevaporated to dryness
  4. dissolutionthe resulting residue was dissolved in methanol (20 mL)
  5. additionThis methanolic solution was treated with 10% palladium on carbon (5 mg, 50% wet)
  6. stirringstirred for 30 min
  7. customevaporated to dryness
  8. custompartitioned between 10% aqueous potassium carbonate (20 mL) and methylene chloride (20 mL)
  9. customThe organic layer was separated
  10. dry with materialdried over sodium sulfate
  11. filtrationFiltration of the organic layer
  12. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-1a3a8fb10c394f95b679c6def17d27bf
Source dataset
uspto-grants-2014_07
Patent number
US08779131B2

Reaction notes

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