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Sodium borohydride → HCID 118318878, Verbindung

HRID 921231
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 921231
[CH2:1]([O:4][C:5]1([CH3:51])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH2:20][N:21]([CH:36]4[CH2:38][CH2:37]4)[CH2:22][C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=4[O:30][C@H:31]([CH2:33][CH:34]=C)[CH3:32])[CH:19]=[C:15]3[N:14]=[C:13]([CH3:39])[C:12]=2[C@H:40]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:7][CH2:6]1)[CH:2]=C.[BH4-].[Na+]>C(Cl)Cl.O>[C:47]([O:46][C@@H:40]([C:12]1[C:13]([CH3:39])=[N:14][C:15]2=[CH:19][C:18]3=[N:17][N:16]2[C:11]=1[N:8]1[CH2:7][CH2:6][C:5]([CH3:51])([O:4][CH2:1][CH2:2][CH2:34][CH2:33][C@H:31]([CH3:32])[O:30][C:24]2[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:23]=2[CH2:22][N:21]([CH:36]2[CH2:37][CH2:38]2)[CH2:20]3)[CH2:10][CH2:9]1)[C:41]([O:43][CH2:44][CH3:45])=[O:42])([CH3:50])([CH3:49])[CH3:48]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 118318877HCID 118318877, Verbindung

Produkt 1

HCID 118318878HCID 118318878, VerbindungAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-((cyclopropyl(4-methyl-2-((S)-pent-4-en-2-yloxy)benzyl)amino)methyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (90 mg, 0.128 mmol) and Grubb's II catalyst (10.89 mg, 0.013 mmol) in DCM (80 mL) was refluxed for 2 h. It was then concentrated and the residue was dissolved in MeOH (2 mL). NaBH4 (4.85 mg, 0.128 mmol) was added and the reaction was stirred at rt for 1 h. It was then diluted with water, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 25% EtOac/hexane to obtain ethyl (2S)-2-(tert-butoxy)-2-[(20S)-11-cyclopropyl-4,16,20,26-tetramethyl-19,25-dioxa-1,5,7,8,11-pentaazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl]acetate (90 mg, 0.107 mmol, 83% yield) as a white solid. LCMS (M+1)=676.4.

Aufarbeitung

  1. temperaturewas refluxed for 2 h
  2. concentrationIt was then concentrated
  3. dissolutionthe residue was dissolved in MeOH (2 mL)
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain an oil, which
  9. customwas then purified by biotage
  10. washeluting with 25% EtOac/hexane

Quellen und Nachweise

ORD-Eintrag
ord-98efac9be6a24328868f68106f6e1468
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09273067B2

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