Acetaldehyde → HCID 131728473, compound

HRID 1927490Notes

Reaction equation

HRID 1927490 reaction equation
[CH:1](=O)[CH3:2].[CH3:4][O:5][C:6]([C:8]1[CH:9]=[C:10]([CH3:35])[C:11]2[O:17][C:16]3[C:18]([Cl:31])=[CH:19][C:20]([NH:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:21][C:15]=3[CH2:14][S:13](=[O:33])(=[O:32])[C:12]=2[CH:34]=1)=[O:7].C(O)(C(F)(F)F)=O.C([BH3-])#N.[Na+]>CO>[CH3:4][O:5][C:6]([C:8]1[CH:9]=[C:10]([CH3:35])[C:11]2[O:17][C:16]3[C:18]([Cl:31])=[CH:19][C:20]([N:22]([CH2:1][CH3:2])[CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]4)=[CH:21][C:15]=3[CH2:14][S:13](=[O:32])(=[O:33])[C:12]=2[CH:34]=1)=[O:7]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 131728472HCID 131728472, compound

Product 1

HCID 131728473HCID 131728473, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetaldehyde (0.151 g, 3.4 mmol) was added to a solution of Example 92k (0.330 g, 0.68 mmol) in MeOH (10 mL) at 0° C. TFA (0.08 g, 0.68 mmol) was then added and stirring continued for 2 h. The reaction mixture was brought to room temperature, treated with sodium cyanoborohydride (0.108 g, 1.7 mmol) and allowed to stir for 4 h. It was concentrated, treated with aqueous sodium bicarbonate solution, water and extracted ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography to obtain the title compound. Yield: 0.80 g, (51%); 1H NMR (CDCl3): δ 1.20 (t, 2H, CH2), 1.70 (t, 2H, CH2), 1.80 (t, 4H, 2CH2), 2.70 (s, 3H, CH3), 2.80 (s, 2H, CH2), 2.90 (m, 2H, CH2), 3.40 (q, 2H, CH2), 3.80 (t, 2H, CH2), 3.9 (s, 3H, OCH3), 4.8 (s, 2H, CH2), 6.8 (s, 2H, Ar), 8.10 (s, 1H, Ar), 8.4 (s, 1H, Ar); MS: m/e (ES−) 506 (M−1).

Workup

  1. customwas brought to room temperature
  2. stirringto stir for 4 h
  3. concentrationIt was concentrated
  4. additiontreated with aqueous sodium bicarbonate solution, water
  5. extractionextracted ethyl acetate
  6. washThe organic layer was washed with water, brine
  7. customdried
  8. concentrationconcentrated
  9. custompurified

Sources & evidence

ORD record
ord-7041da9a900c4f4db743bbdc6966cb38
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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