Acetaldehyde → HCID 9868894, compound

HRID 480256Notes

Reaction equation

HRID 480256 reaction equation
O[C:2]([C:4](F)(F)F)=O.[NH2:8][CH2:9][CH:10]([NH:14][C:15](=[O:33])[CH:16]([CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[CH2:17][C:18]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:19])[C:11](=O)[NH2:12].[C:34]1(=O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)C>C1COCC1>[C:9]([CH:10]([CH2:11][N:12]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[CH2:2][CH3:4])[NH:14][C:15](=[O:33])[CH:16]([CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[CH2:17][C:18]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:19])#[N:8]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 86583981HCID 86583981, compound

Product 1

HCID 9868894HCID 9868894, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the above N-(2-Amino-1-carbamoyl-ethyl)-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyramide TFA salt (0.154 g, 0.32 mmol) in 10 mL THF was added cyclohexanone (0.62 g, 0.64 mmol). The reaction was cooled to 0° C. and sodium triacetoxyborohydride was added (0.176 g, 0.83 mmol) and the reaction was allowed to warm up to room temperature overnight. The reaction mixture was cooled in an ice bath and acetaldehyde (0.1 mL, excess) was added. The ice bath was removed and the reaction was stirred for 2 h. The reaction was quenched with saturated sodium bicarbonate solution, extracted with EtOAc and dried over anhydrous sodium sulfate. The volatiles were removed and the crude product was purified by flash column chromatography (SiO2, 5% MeOH in CH2Cl2) to give the desired product (0.1 g, 65.5%). MS: m/z=479 M+1.

Workup

  1. temperatureto warm up to room temperature overnight
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. customThe ice bath was removed
  4. customThe reaction was quenched with saturated sodium bicarbonate solution
  5. extractionextracted with EtOAc
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe volatiles were removed
  8. customthe crude product was purified by flash column chromatography (SiO2, 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1adfab20c8ab4b00a9ccabba245d5173
Source dataset
uspto-grants-2003_11
Patent number
US06649642B2

Reaction notes

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