Acetaldehyde → Benzyl-N-(1-cyanoethyl)glycine hydrochloride

HRID 322543

Reaktionsgleichung

Reaktionsgleichung von HRID 322543
[Si]([C:5]#[N:6])(C)(C)C.[CH2:7]([NH:14][CH2:15][C:16]([OH:18])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[ClH:19].[CH:20](=O)[CH3:21].CCO>C(Cl)Cl>[ClH:19].[CH2:7]([N:14]([CH:20]([C:5]#[N:6])[CH3:21])[CH2:15][C:16]([OH:18])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

7

Edukt 5

HCID 177AcetaldehydeHCID 313Hydrochloric Acid2×HCID 702EthanolHCID 82115Trimethylsilyl cyanideHCID 869652-(Benzylamino)acetic acid

Produkt 1

HCID 68560147Benzyl-N-(1-cyanoethyl)glycine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TMSCN (18.8 mL, 141 mmol) was added cautiosly to a stirred solution of benzylglycine free base (23.3 g 141 mmol—from the HCl salt by partition between EtOAc and brine basified with saturated Na2CO3 solution) and acetaldehyde (7.88 mL, 141 mmol) in CH2Cl2 (50 mL). After 4 h the volatiles were removed in vacuo and the residue was taken up in EtOAc and washed with brine, dried (Na2SO4) and evaporated in vacuo to an oil. The oil was redissolved in EtOAc and 9.9 M HCl in EtOH (15.25 mL, 151 mmol) was added to give a crystalline precipitate which was isolated by filtration, washing with EtOAc and Et2O to give the title compound (18-2):

Aufarbeitung

  1. customby partition between EtOAc and brine
  2. customAfter 4 h the volatiles were removed in vacuo
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo to an oil
  6. dissolutionThe oil was redissolved in EtOAc
  7. customto give a crystalline precipitate which
  8. customwas isolated by filtration
  9. washwashing with EtOAc and Et2O

Quellen und Nachweise

ORD-Eintrag
ord-f2fe9df0a04c43a5b049b951bd2656a9
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211184B1

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