Acetaldehyde → HCID 131728467, compound

HRID 1927484Notes

Reaction equation

HRID 1927484 reaction equation
F[C:2](F)(F)[C:3](O)=O.[CH3:8][O:9][C:10]([C:12]1[CH:13]=[C:14]([CH3:40])[C:15]2[O:21][C:20]3[C:22]([Cl:36])=[CH:23][C:24]([NH:26][CH2:27][CH2:28][NH:29][CH2:30][C:31]4[O:32][CH:33]=[CH:34][CH:35]=4)=[CH:25][C:19]=3[CH2:18][S:17](=[O:38])(=[O:37])[C:16]=2[CH:39]=1)=[O:11].[CH:41](=O)[CH3:42].C([BH3-])#N.[Na+]>CO.O>[CH3:8][O:9][C:10]([C:12]1[CH:13]=[C:14]([CH3:40])[C:15]2[O:21][C:20]3[C:22]([Cl:36])=[CH:23][C:24]([N:26]([CH2:2][CH3:3])[CH2:27][CH2:28][N:29]([CH2:41][CH3:42])[CH2:30][C:31]4[O:32][CH:33]=[CH:34][CH:35]=4)=[CH:25][C:19]=3[CH2:18][S:17](=[O:38])(=[O:37])[C:16]=2[CH:39]=1)=[O:11]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 131728466HCID 131728466, compound

Product 1

HCID 131728467HCID 131728467, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Trifluoroacetic acid (0.03 mL, 0.4 mmol) was added to mixture of Example 84k (0.2 g, 0.40 mmol) and acetaldehyde (0.115 mL, 2 mmol) in dry methanol (10 mL) at 0° C. The reaction mixture was stirred at room temperature in an atmosphere of nitrogen for 1.5 h. It was treated with sodium cyanoborohydride (0.064 g, 1 mmol), stirred for 1.5 h, treated with cold water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried and purified using flash chromatography (silica gel, ethyl acetate/pet ether) to obtain the title compound as a white solid. Yield: 0.285 g, (68.69%); 1H NMR (DMSO-d6): δ 1.1 (t, 6H, 2CH3), 2.60-2.69 (m, 4H, 2CH2), 2.70 (s, 3H, CH3), 3.30-3.40 (m, 4H, 2CH2), 3.70 (s, 2H, CH2), 3.95 (s, 3H, OCH3), 4.65 (s, 2H, CH2), 6.25-6.85 (m, 3H, Ar), 6.65 (s, 1H, Ar), 7.45 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.50 (s, 1H, Ar); MS: m/e (CI+) 547 (M+1).

Workup

  1. stirringstirred for 1.5 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. custompurified

Sources & evidence

ORD record
ord-93193f602f664b68bc3cb971896593bb
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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