Hydrochloric Acid → (2R)-3-[3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]-2-[(phenylsulfonyl)-amino]propanoic Acid

HRID 724664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724664
FC(F)(F)C(O)=O.[NH2:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]2)=[C:17]([Br:29])[CH:16]=1)[C:10]([O:12]C)=[O:11].C(N(CC)CC)C.[C:37]1([S:43](Cl)(=[O:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[OH-].[Li+].Cl>CO.O>[Br:29][C:17]1[CH:16]=[C:15]([CH2:14][C@@H:9]([NH:8][S:43]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:45])=[O:44])[C:10]([OH:12])=[O:11])[CH:20]=[CH:19][C:18]=1[CH:21]1[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 11670631Methyl (2S)-2-amino-3-[3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]-propanoate Trifluoroacetate

Produkt 1

HCID 69597645(2R)-3-[3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]-2-[(phenylsulfonyl)-amino]propanoic AcidAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

Methyl (2S)-2-amino-3-[3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)-phenyl]-propanoate trifluoroacetate (77.1 mg, 0.152 mmol) in methanol (1.7 mL,) was treated with triethylamine (85.0 μL, 0.610 mmol) and then benzenesulfonyl chloride (29.2 μL, 0.228 mmol). The solution was stirred at rt for 2 h. 4 M lithium hydroxide in water (0.38 mL) was added and stirred for 3 h at rt. The solution was acidified with aqueous 1 N hydrochloric acid solution (4 mL), diluted with methanol (1.5 mL) and purified by preparative LCMS to afford product as a white solid (55.4 mg, 70%). 1H NMR (400 MHz, CD3OD): δ 7.65–7.62 (m, 2H), 7.53–7.36 (m, 4H), 7.25–7.20 (m, 1H), 5.65 (t, J=6.8 Hz, 1H), 4.06–5.01 (m, 1H), 3.48 (dd, J=16.2, 8.0 Hz, 1H), 3.38–3.28 (m, 1H), 3.11–3.06 (m, 1H), 2.87–2.83 (m, 1H); LCMS found for C18H18BrN2O7S2 (M+H)+: m/z=517.

Aufarbeitung

  1. stirringstirred for 3 h at rt
  2. custompurified by preparative LCMS

Quellen und Nachweise

ORD-Eintrag
ord-fd98c279e8074310afce4367d104a61a
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141596B2

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