Dimethylethylamine → HCID 86762230, Verbindung

HRID 338129

Reaktionsgleichung

Reaktionsgleichung von HRID 338129
[C:1]([NH:9][C:10]1[S:11][CH2:12][CH:13]2[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:16][C:14]2([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C(#N)C.CN(C)CC>C(=O)=O>[C:1]([NH:9][C:10]1[S:11][CH2:12][C@@H:13]2[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:20])[CH2:16][C@:14]2([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11723DimethylethylamineHCID 21959252Acetonitrile methanolHCID 89832302HCID 89832302, Verbindung

Produkt 1

HCID 86762230HCID 86762230, VerbindungAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 280Carbon DioxideLösungsmittel

Versuchsvorschrift

Racemic benzyl 2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (30 g, 63 mmol) is chirally purified by SFC: (Column: Chiralpak IC 2.1×25 cm; eluent: 40% methanol/acetonitrile (8/2) with 0.2% dimethylethyl amine in CO2; flow: 70 mL/min at UV 284 nm). The second eluting isomer is the title compound (11.1 g, 37%, >98% ee). Chiral analysis of the isolated isomer 2: Chiralpak IC 0.46×10 cm, 5 μm; eluent: 40% methanol/acetonitrile (8/2) with 0.2% dimethyl ethyl amine in CO2; flow: 5 mL/min at UV 215 nm. Rt=3.2 minutes. [α]D20=−88 (C=1.0, methanol), ES/MS (m/e) 372 (M+H)

Quellen und Nachweise

ORD-Eintrag
ord-b3e03c3bf2a14cd99f884f15258ef18c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889856B2

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