Tert-Butylamine → Boc-Hyp-NH-tBu

HRID 1780274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1780274
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.[C:30]([O:34][C:35]([N:37]1[CH2:44][C@@H:43]([OH:45])[CH2:42][C@H:38]1[C:39](O)=[O:40])=[O:36])([CH3:33])([CH3:32])[CH3:31]>CN(C)C=O>[C:30]([O:34][C:35]([N:37]1[CH2:44][C@H:43]([OH:45])[CH2:42][C@H:38]1[C:39]([NH:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:40])=[O:36])([CH3:33])([CH3:31])[CH3:32]

Komponenten

6

Edukt 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 688614(2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Produkt 1

HCID 10334194Boc-Hyp-NH-tBuAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

17.16 g (62.40 mmol) of diphenylphosphoryl azide, 5.70 g (78.08 mmol) of t-butylamine and 10.4 g (104.00 mmol) of triethylamine were added, in that order, to a solution of 12.0 g (51.95 mmol) of (4S)-1-t- butoxycarbonyl-4-hydroxy-L-proline in 100 ml of dimethylformamide, whilst ice-cooling, and the mixture was stirred for 5 hours. At the end of this time, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic extract was washed with a 10% w/v aqueous solution of citric acid, with a 10% w/v aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which the mixture was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was recrystallized from ethyl acetate, to give 10.0 g of the title compound as colorless crystals, melting at 192°-193° C.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with a 10% w/v aqueous solution of citric acid, with a 10% w/v aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialafter which the mixture was dried over anhydrous sodium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure
  7. customthe resulting residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a2a828df3e484db7aa1e5ba20b5e00d7
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05629406

Notizen zur Reaktion

Wird geladen…