Benzyl chloroformate → (7S,10S,13S)-13-Benzyloxycarbonylamino-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo-[13.2.2]nonadeca-1(18),15(19),16-triene-7-carboxylic acid methyl ester

HRID 2371327

Reaktionsgleichung

Reaktionsgleichung von HRID 2371327
Cl.[CH3:2][O:3][C:4]([C@H:6]1[NH:22][C:21](=[O:23])[C@H:20](C(C)C)[NH:19][C:18](=[O:27])[C@@H:17]([NH2:28])[CH2:16][C:15]2=[CH:29][CH:30]=[C:12]([CH:13]=[CH:14]2)[O:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].Cl[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].CCN([CH:48]([CH3:50])[CH3:49])C(C)C.[CH3:51]COC(C)=O.C(Cl)Cl>CN(C=O)C>[CH3:2][O:3][C:4]([C@H:6]1[NH:22][C:21](=[O:23])[C@H:20]([CH2:49][CH:48]([CH3:50])[CH3:51])[NH:19][C:18](=[O:27])[C@@H:17]([NH:28][C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:16][C:15]2=[CH:29][CH:30]=[C:12]([CH:13]=[CH:14]2)[O:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5]

Komponenten

6

Edukt 4

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 21226138Dichloromethane ethylacetateHCID 86650244(7S,10S,13S)-13-Amino-10-isopropyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1-(18),15(19),16-triene-7-carboxylic acid methyl ester hydrogen chloride salt

Produkt 1

HCID 44191155(7S,10S,13S)-13-Benzyloxycarbonylamino-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo-[13.2.2]nonadeca-1(18),15(19),16-triene-7-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Amine 47 (65 mg) was dissolved in anhydrous DMF (30 mL). Benzyl chloroformate (0.29 mL) and DIPEA (0.75 mL) were added and the reaction mixture was stirred at rt for 18 h before being partitioned between chloroform and 1M hydrochloric acid. The aqueous phase was extracted three more times with chloroform and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 15% EtOAc/DCM to 50% EtOAc/DCM to yield an off-white solid, 54 mg, 70%. Rf=0.33 (30% EtOAc/DCM).

Aufarbeitung

  1. custombefore being partitioned between chloroform and 1M hydrochloric acid
  2. extractionThe aqueous phase was extracted three more times with chloroform
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. washeluting with a gradient of 15% EtOAc/DCM to 50% EtOAc/DCM
  8. customto yield an off-white solid, 54 mg, 70%

Quellen und Nachweise

ORD-Eintrag
ord-028affbd831f4a298fda6f3bde9da8b2
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710178B2

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