Acetaldehyde, 2,2-dimethoxy- → HCID 58504215, compound

HRID 2407785Notes

Reaction equation

HRID 2407785 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:29])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[S:22][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[N:20][CH:19]=2)[CH2:13][CH2:12]1.[CH3:30][O:31][CH:32]([O:35][CH3:36])[CH:33]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O.C(OCC)(=O)C>[CH3:30][O:31][CH:32]([O:35][CH3:36])[CH2:33][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:29])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[S:22][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[N:20][CH:19]=2)[CH2:13][CH2:12]1

Participants

7

Reactant 3

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 5049666Sodium triacetoxyborohydrideHCID 58504086HCID 58504086, compound

Product 1

HCID 58504215HCID 58504215, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound prepared in Example 309 (0.613 g) was suspended in 1,2-dichloroethane (30 mL). 2,2-Dimethoxyacetaldehyde solution in water (60% by weight) (2.28 mL) and beaded molecular sieves were added and the reaction mixture stirred at room temperature for 4 hours. Sodium triacetoxyborohydride (2.62 g) was added and the reaction mixture stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 2% (9:1 methanol/concentrated ammonium hydroxide)/dichloromethane) to furnish the title compound (0.555 g) with the following physical properties.

Workup

  1. additionwere added
  2. stirringthe reaction mixture stirred at room temperature overnight
  3. washwashed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude material, which
  8. customwas purified by flash column chromatography (eluant: 2% (9:1 methanol/concentrated ammonium hydroxide)/dichloromethane)

Sources & evidence

ORD record
ord-10c6f6b9acbd450a90d1156e98a26b84
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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