1-Hydroxybenzotriazole → Benzyl(E,4S)-4-[(2-hydroxydodecanoyl)amino]oct-2-enoate

HRID 19961

Reaktionsgleichung

[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]CCCC)[C:3]([OH:5])=O.[Cl-].[CH2:21]([O:28][C:29](=[O:38])/[CH:30]=[CH:31]/[C@@H:32]([NH3+:37])[CH2:33][CH2:34][CH2:35][CH3:36])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CCN(CC)CC>[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3]([NH:37][C@@H:32]([CH2:33][CH2:34][CH2:35][CH3:36])/[CH:31]=[CH:30]/[C:29]([O:28][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:38])=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a stirred solution of 2-hydroxyhexadecanoic acid (0.54 g, 2.0 mmol) and (E,4S)-1-(benzyloxy)-1-oxooct-2-en-4-aminium chloride (0.28 g, 1.0 mmol) in CH2Cl2 (5 mL), Et3N (0.3 mL) and subsequently WSCI (0.57 g, 3.0 mmol) and HOBt (0.32 g, 2.0 mmol) were added at 0° C. The reaction mixture was stirred for 1 h at 0° C. and at room temperature for 1 day. The organic layer was washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography (CHCl3/MeOH 98/2). Yield 0.33 g (75%); [α]D−10.3 (c 0.5 CHCl3);

Aufarbeitung

washThe organic layer was washed with brine
dry with materialdried over Na2SO4
customevaporated under reduced pressure
customThe residue was purified by column chromatography (CHCl3/MeOH 98/2)

Quellen und Nachweise

ORD-Eintrag: ord-0c3ba59a99b847c38d097cd9d1dc0b68
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745489B2

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