Formaldehyde → 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[N-(4-cyanophenylmethyl)-N-methylamino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine

HRID 1829107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1829107
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:23]([N:25]1[CH2:29][CH2:28][S:27][CH2:26]1)=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[C:32](C1C=CC(CN[C@@H]2CN[C@H](C(N3CCSC3)=O)C2)=CC=1)#N.C=O.C([BH3-])#N.[Na+]>C(#N)C.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH3:32])[CH2:10][C@H:9]1[C:23]([N:25]1[CH2:29][CH2:28][S:27][CH2:26]1)=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 675066143-[(2S,4S)-1-tert-Butoxycarbonyl-4-(4-cyanophenylmethyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidineHCID 675078123-[(2S,4S)-4-(4-cyanophenylmethyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidine dihydrochloride

Produkt 1

HCID 675071013-{(2S,4S)-1-tert-butoxycarbonyl-4-[N-(4-cyanophenylmethyl)-N-methylamino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-[(2S,4S)-1-tert-Butoxycarbonyl-4-(4-cyanophenylmethyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidine [product of Example 63 (1), 1.35 g] and 37% formaldehyde solution (0.788 mL) were dissolved in acetonitrile (20 mL), and the mixture was stirred at room temperature for 30 min. Sodium cyanoborohydride (0.305 g) and several drops of acetic acid were added to the reaction mixture, and the reaction mixture was stirred for 1 hr. The reaction mixture was evaporated under reduced pressure. Saturated aqueous sodium hydrogencarbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[N-(4-cyanophenylmethyl)-N-methylamino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine (0.953 g) as white amorphous.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 1 hr
  2. customThe reaction mixture was evaporated under reduced pressure
  3. additionSaturated aqueous sodium hydrogencarbonate solution was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe extract was dried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-63f9f6195f9746d39ec984762e2960c7
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07060722B2

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