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4-Methylmorpholine → tert-butyl (4S,7S,10aS)-7-carbamoyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

HRID 529484
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 529484
ClC(OCC(C)C)=O.[C:9]([O:13][C:14]([NH:16][C@H:17]1[CH2:23][CH2:22][S:21][C@H:20]2[CH2:24][CH2:25][CH2:26][C@@H:27]([C:28]([OH:30])=O)[N:19]2[C:18]1=[O:31])=[O:15])([CH3:12])([CH3:11])[CH3:10].C[N:33]1CCOCC1.[NH4+].[OH-]>C(Cl)Cl>[C:28]([C@H:27]1[N:19]2[C@@H:20]([S:21][CH2:22][CH2:23][C@H:17]([NH:16][C:14](=[O:15])[O:13][C:9]([CH3:11])([CH3:10])[CH3:12])[C:18]2=[O:31])[CH2:24][CH2:25][CH2:26]1)(=[O:30])[NH2:33]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 68292173(4S,7S,10aS)-4-(tert-butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid

Produkt 1

HCID 68311221tert-butyl (4S,7S,10aS)-7-carbamoyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate
Ausbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Isobutyl chloroformate (31.2 mg, 0.229 mmol) was added to a solution of (4S,7S,10aS)-4-(tert-Butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid (75 mg, 0.22 mmol) and 4-methylmorpholine (26.4 mg, 0.261 mmol) in DCM at 0° C. After stirring for 30 min at 0° C., NH4OH was added. The ice bath was removed and the reaction mixture was stirred at rt for 30 min. The reaction mixture was concentrated and the residue was partitioned between EtOAc and aqueous 0.5 N HCl. The organic phase was isolated, washed with saturated aqueous NaHCO3 and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give tert-butyl (4S,7S,10aS)-7-carbamoyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (67 mg, 0.20 mmol, 90% yield) as an oil. Anal. Calcd. for C15H25N3O4S m/z 343.4. found: 344.3 (M+H)+.

Aufarbeitung

  1. customThe ice bath was removed
  2. stirringthe reaction mixture was stirred at rt for 30 min
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was partitioned between EtOAc and aqueous 0.5 N HCl
  5. customThe organic phase was isolated
  6. washwashed with saturated aqueous NaHCO3 and saturated aqueous NaCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c46ac038bc664915900f0838e807ddd1
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09346852B2

Notizen zur Reaktion

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