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Ethyl Acetate → 1H-Pyrrole-2-carboxylic acid ((7S,10S,13S)-7-formyl-10-isopropyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-13-yl)-amide

HRID 2371329
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2371329
C[O:2][C:3]([C@H:5]1[NH:21][C:20](=[O:22])[C@H:19]([CH:23]([CH3:25])[CH3:24])[NH:18][C:17](=[O:26])[C@@H:16]([NH:27][C:28]([C:30]2[NH:31][CH:32]=[CH:33][CH:34]=2)=[O:29])[CH2:15][C:14]2=[CH:35][CH:36]=[C:11]([CH:12]=[CH:13]2)[O:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=O.CC(C[AlH]CC(C)C)C.CCOC(C)=O>C(Cl)Cl>[CH:3]([C@H:5]1[NH:21][C:20](=[O:22])[C@H:19]([CH:23]([CH3:25])[CH3:24])[NH:18][C:17](=[O:26])[C@@H:16]([NH:27][C:28]([C:30]2[NH:31][CH:32]=[CH:33][CH:34]=2)=[O:29])[CH2:15][C:14]2=[CH:13][CH:12]=[C:11]([CH:36]=[CH:35]2)[O:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 66846964(7S,10S,13S)-10-Isopropyl-9,12-dioxo-13-[(1H-pyrrole-2-carbonyl)-amino]-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-7-carboxylic acid methyl ester

Produkt 1

HCID 866502451H-Pyrrole-2-carboxylic acid ((7S,10S,13S)-7-formyl-10-isopropyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-13-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Ester 51 (45 mg) was dissolved in DCM (6 mL) under an atmosphere of argon. The reaction was cooled to −78° C. To the resultant solution DIBAL (0.5 mL) was added dropwise. This was stirred for 2 h before being allowed to warm to rt overnight. The reaction mixture was partitioned between EtOAc and 1M hydrochloric acid. The aqueous phase was extracted again with EtOAc and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 1/1 EtOAc/(50/70) petroleum ether to EtOAc to yield a light brown solid, 14 mg, 33%. Rf=0.25 (1/1 EtOAc/(50/70) petroleum ether).

Aufarbeitung

  1. temperatureto warm to rt overnight
  2. customThe reaction mixture was partitioned between EtOAc and 1M hydrochloric acid
  3. extractionThe aqueous phase was extracted again with EtOAc
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification
  8. washeluting with a gradient of 1/1 EtOAc/(50/70) petroleum ether to EtOAc
  9. customto yield a light brown solid, 14 mg, 33%

Quellen und Nachweise

ORD-Eintrag
ord-ab217bbab05b4c32a1382387a05c8810
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08710178B2

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