Acetaldehyde → HCID 131728471, compound

HRID 1927488Notes

Reaction equation

HRID 1927488 reaction equation
F[C:2](F)(F)[C:3](O)=O.[CH3:8][O:9][C:10]([C:12]1[CH:13]=[C:14]([CH3:41])[C:15]2[O:21][C:20]3[C:22]([Cl:37])=[CH:23][C:24]([NH:26][CH2:27][CH2:28][NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:25][C:19]=3[CH2:18][S:17](=[O:39])(=[O:38])[C:16]=2[CH:40]=1)=[O:11].[CH:42](=O)[CH3:43].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO>[CH3:8][O:9][C:10]([C:12]1[CH:13]=[C:14]([CH3:41])[C:15]2[O:21][C:20]3[C:22]([Cl:37])=[CH:23][C:24]([N:26]([CH2:27][CH2:28][N:29]([CH2:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:2][CH3:3])[CH2:42][CH3:43])=[CH:25][C:19]=3[CH2:18][S:17](=[O:39])(=[O:38])[C:16]=2[CH:40]=1)=[O:11]

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 131728470HCID 131728470, compound

Product 1

HCID 131728471HCID 131728471, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (0.1 mL, 1.32 mmol) was added to a solution of Example 88k (0.28 g, 0.56 mmol) in methanol (15 mL) at 0° C. Acetaldehyde (2 mL) was added and stirring continued for 2 h. The reaction mixture was brought to room temperature, treated with sodium cyanoborohydride (0.203 g, 2.96 mmol) and allowed to stir overnight. It was then treated with an aqueous sodium bicarbonate solution and cooled to 0° C. The precipitated solid was filtered, washed with methanol, dried and purified using flash chromatography (silica gel, 0.5% methanol/chloroform) to obtain the title compound. Yield: 0.21 g, (67.5%); 1H NMR (CDCl3): δ 1.1 (m, 6H, 2CH3), 2.6 (m, 4H, 2CH2), 2.6 (s, 3H, CH3), 3.22 (t, 2H, CH2), 3.25 (t, 2H, CH2), 3.65 (s, 2H, CH2), 3.9 (s, 3H, OCH3), 4.53 (s, 2H, CH2), 6.22 (s, 1H, Ar), 6.52 (s, 1H, Ar), 7.35 (m, 5H, Ar), 8.1 (s, 1H, Ar), 8.45 (s, 1H, Ar); MS: m/e (ES+) 556 (M+1).

Workup

  1. customwas brought to room temperature
  2. stirringto stir overnight
  3. filtrationThe precipitated solid was filtered
  4. washwashed with methanol
  5. customdried
  6. custompurified

Sources & evidence

ORD record
ord-d0e0ffed843f42c585469f65f9fdc290
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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