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Lithium diisopropylamide → HCID 89463048, Verbindung

HRID 1473208
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1473208
C([N:8]1[C:12]2[C:13](=[O:34])[N:14]([CH3:33])[C:15]([CH:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:25]([OH:27])=[O:26])=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[C:11]=2[CH:10]=[CH:9]1)C1C=CC=CC=1.[Li+].CC([N-]C(C)C)C.CCCCCCC.O1CCCC1.C(C1C=CC=CC=1)C>O1CCCC1>[C:29]([O:28][CH:24]([C:15]1[N:14]([CH3:33])[C:13](=[O:34])[C:12]2[NH:8][CH:9]=[CH:10][C:11]=2[C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1)[C:25]([OH:27])=[O:26])([CH3:32])([CH3:31])[CH3:30]
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Komponenten

5

Edukt 3

HCID 2724682Lithium diisopropylamide2×HCID 22742125Tetrahydrofuran heptane ethylbenzolHCID 71538481HCID 71538481, Verbindung

Produkt 1

HCID 89463048HCID 89463048, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

An ice cold mixture of 2-(1-benzyl-6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetic acid (200 mg, 0.423 mmol) in Tetrahydrofuran (THF) (2.0 mL) was treated with dropwise addition of LDA, 2M solution in heptane/THF/ethylbenzene (0.423 mL, 0.846 mmol) and then allowed to stir at 0° C. for 20 minutes. Additional LDA (0.212 mL, 0.423 mmol) was added and then stirred an additional 20 minutes. The mixture was quenched by adding 1N HCl, acidified to pH 2 and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to give the crude debenzylation product which was used crude in the next step. LC/MS (m/z) ES+=369 (M+1).

Aufarbeitung

  1. stirringstirred an additional 20 minutes
  2. customThe mixture was quenched
  3. additionby adding 1N HCl
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude debenzylation product which

Quellen und Nachweise

ORD-Eintrag
ord-f0b0812391a745cb9ba1dbd32b2d8426
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012642B2

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