Tetrahydrofuran → HCID 9846186, compound

HRID 840385Notes

Reaction equation

HRID 840385 reaction equation
C([C:4]#[N:5])(=O)C.[CH2:6]([N:13]([C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C@H:14]([CH:22]=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O:34]1CC[CH2:36][CH2:35]1>[Cl-].[Zn+2].[Cl-]>[CH2:6]([N:13]([C@@H:14]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:22]([O:23][C:35](=[O:34])[CH3:36])[C:4]#[N:5])[C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 694302-OxopropiononitrileHCID 15887289HCID 15887289, compound

Product 1

HCID 9846186HCID 9846186, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Acetyl cyanide (4.55 ml, 64.3 mmol) was added to a mixture of N-benzyl-N-benzyloxycarbonyl-L-phenylalaninal (20.0 g, 53.6 mmol), zinc chloride (8.76 g, 64.3 mmol) and tetrahydrofuran (70 ml) at 5° C. with stirring, and the whole was stirred at 25° C. for 12 hours. After the reaction was finished, tetrahydrofuran was evaporated under reduced pressure. Water was added to the residue, and the whole was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 19.6 g (yield 83%, erythro:threo=94:6) of titled (2S, 3S)-3-[N-(benzyl)-N-(benzyloxycarbonyl) amino]-2-acetyloxy-4-phenylbutyronitrile.

Workup

  1. stirringthe whole was stirred at 25° C. for 12 hours
  2. customtetrahydrofuran was evaporated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe whole was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3a4d3ba17dd24a73b8eb1b8917631480
Source dataset
uspto-grants-2002_04
Patent number
US06365754B1

Reaction notes

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