Dichloromethane → Tert-butyl (2S,3R)-4-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-1-(3-fluorophenyl)-3-hydroxybutan-2-ylcarbamate

HRID 1009145

Reaktionsgleichung

Reaktionsgleichung von HRID 1009145
[Si]([O:8][C@H:9]([CH2:27][NH:28][C@@H:29]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH:37]=2)[NH:32][C:31]([CH3:45])([CH3:44])[CH2:30]1)[C@@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)(C(C)(C)C)(C)C.C(Cl)Cl.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>O>[CH3:44][C:31]1([CH3:45])[CH2:30][C@H:29]([NH:28][CH2:27][C@@H:9]([OH:8])[C@@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH:37]=2)[NH:32]1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86614130Tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-4-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-1-(3-fluorophenyl)butan-2-ylcarbamate

Produkt 1

HCID 86614131Tert-butyl (2S,3R)-4-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-1-(3-fluorophenyl)-3-hydroxybutan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl(2S,3R)-3-(tert-butyldimethylsilyloxy)-4-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-1-(3-fluorophenyl)butan-2-ylcarbamate (0.231 g, 0.360 mmol) in DCM (1.20 ml, 0.360 mmol) was added tetrabutylammonium fluoride (1.44 ml, 1.44 mmol). The resulting solution was stirred overnight. The mixture was transferred to a sep. funnel containing EtOAc and H2O. The aqueous layer was washed 4× with EtOAc. The proganic layers were combined, dried over MgSO4, filtered and concentrated. The crude mixture was purified by the MPLC. MS m/z: 528 (M+1).

Aufarbeitung

  1. washThe aqueous layer was washed 4× with EtOAc
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude mixture was purified by the MPLC

Quellen und Nachweise

ORD-Eintrag
ord-8e2b475f37c44e7e9ea238a48335c098
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973047B2

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