Formaldehyde → HCID 69444662, Verbindung

HRID 1271715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271715
C(O[C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C@H:10]([NH:25][C:26](=[O:40])[C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]3=[O:39])=[CH:29][CH:28]=2)[CH2:9]1)=O)(C)(C)C.C(Cl)Cl.C=O.[BH3-]C#N.[Na+]>C(O)(C(F)(F)F)=O.O.CC#N.CC(O)=O.CO>[CH2:18]([O:17][C:15](=[O:16])[NH:14][C@H:11]1[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][C@H:10]1[NH:25][C:26](=[O:40])[C:27]1[CH:28]=[CH:29][C:30]([N:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]2=[O:39])=[CH:31][CH:32]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

10

Edukt 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 69437112Cis-4-Benzyloxycarbonylamino-3-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 69444662HCID 69444662, VerbindungAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Cis-4-Benzyloxycarbonylamino-3-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester (285 mg, 0.52 mmol) was stirred in TFA (3 mL) and CH2Cl2 (5 mL) at rt for 1.5 h. LC/MS showed completion of the reaction (447.33 (M+H), tR=2.23 min, 10–90% MeOH in H2O with 10 mM NH4OAc in a 4-min run). The solvents were evaporated. Half of the residue (0.26 mmol) was dissolved in CH3CN (2 mL). HCHO (37% wt in H2O, 0.20 mL) was added, followed by the addition of NaCNBH3 (78 mg). The resulting mixture was stirred at rt for 40 min. HOAc was added dropwise to neutralize the mixture. The resulting mixture was stirred for additional 1 h, extracted with EtOAc (3×), dried over MgSO4, filtered, and concentrated to dryness to give crude cis-{1-methyl-3-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-piperidin-4-yl}-carbamic acid benzyl ester (130 mg). Anal. LC/MS (ESI) 461.14 (M+H), tR=2.63 min (10%–90% MeOH in H2O with 10 mM NH4OAc in a 4-min run).

Aufarbeitung

  1. customThe solvents were evaporated
  2. stirringThe resulting mixture was stirred for additional 1 h
  3. extractionextracted with EtOAc (3×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-63bca03985634e86b73940c0c028287c
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205318B2

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