Acetaldehyde → HCID 131728469, compound

HRID 1927486Notes

Reaction equation

HRID 1927486 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[S: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+].C(=O)(O)[O-].[Na+]>CO>[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[S: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 5

HCID 177AcetaldehydeHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 131728468HCID 131728468, compound

Product 1

HCID 131728469HCID 131728469, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Trifluoroacetic acid (0.05 mL, 0.67 mmol) was added to a solution of Example 86k (0.17 g, 0.335 mmol) in methanol (10 mL) at 0° C. Acetaldehyde (1 mL, 19.5 mmol) was added and the reaction mixture was stirred at 0-10° C. for 2 h. The reaction mixture was brought to room temperature, treated with sodium cyanoborohydride (0.092 g, 1.34 mmol) and left stirring overnight. It was treated with an aqueous sodium bicarbonate solution, concentrated, treated with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, 20% ethyl acetate/pet ether) to obtain the title compound. Yield: 0.11 g, (58.3%); 1H NMR (CDCl3): δ 1.1 (q, 6H, 2CH3), 2.62 (t, 4H, 2CH2), 2.65 (s, 3H, CH3), 3.32 (m, 4H, 2CH2), 3.83 (s, 2H, CH2), 3.92 (s, 3H, CH3), 5.2 (s, 2H, CH2), 6.32 (s, 1H, CH2), 6.52 (s, 1H, Ar), 7.00 (m, 2H, Ar), 7.32 (s, 1H, Ar), 8.1 (s, 1H, Ar), 8.45 (s, 1H, Ar); MS: m/e (ES+) 563 (M+1).

Workup

  1. customwas brought to room temperature
  2. waitleft
  3. stirringstirring overnight
  4. concentrationconcentrated
  5. additiontreated with water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water, brine
  8. customdried
  9. concentrationconcentrated
  10. custompurified

Sources & evidence

ORD record
ord-e59f48aa0a5a4dd8ba8779ec820e8b2b
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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