Lithium Hydroxide → tert-butyl 2-(4-chlorophenyl)-2-(6-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzo[d]isothiazol-3-yl)ethylcarbamate

HRID 521395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 521395
[Li+].[OH-].[N+](C1C=CC(C([O:12][C@H:13]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([C:22]4[CH:47]=[CH:46][C:25]5[C:26]([CH:29]([C:39]6[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=6)[CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[N:27][S:28][C:24]=5[CH:23]=4)[C:16]=3[C@H:15]([CH3:48])[CH2:14]2)=O)=CC=1)([O-])=O>C1COCC1>[Cl:45][C:42]1[CH:41]=[CH:40][C:39]([CH:29]([C:26]2[C:25]3[CH:46]=[CH:47][C:22]([C:21]4[C:16]5[C@H:15]([CH3:48])[CH2:14][C@@H:13]([OH:12])[C:17]=5[N:18]=[CH:19][N:20]=4)=[CH:23][C:24]=3[S:28][N:27]=2)[CH2:30][NH:31][C:32](=[O:33])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:44][CH:43]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 67437737HCID 67437737, Verbindung

Produkt 1

HCID 67438914tert-butyl 2-(4-chlorophenyl)-2-(6-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzo[d]isothiazol-3-yl)ethylcarbamateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1N LiOH aqueous solution (0.30 mL, 0.30 mmol) was added to a stirred solution of (5R,7R)-4-(3-(2-(tert-butoxycarbonylamino)-1-(4-chlorophenyl)ethyl)benzo[d]isothiazol-6-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (102 mg, 0.149 mmol) in THF (3 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated. The resulting residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The resulting residue was purified by column chromatography (DCM:MeOH, 60:1) to give tert-butyl 2-(4-chlorophenyl)-2-(6-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzo[d]isothiazol-3-yl)ethylcarbamate (62 mg, 78%) as an oil. LCMS (APCI+) m/z 537, 539 [M+H]+; Rt=3.99 min.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customThe resulting residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography (DCM:MeOH, 60:1)

Quellen und Nachweise

ORD-Eintrag
ord-d5c3e4db8cb84a3fb5e576d59073f00a
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328091B2

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