Hydroxylamine → 6-(2-(9H-fluoren-9-ylidene)acetamido)-N-hydroxyhexanamide

HRID 1926191Notizen

Reaktionsgleichung

[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=O)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(OCC)=O.[NH2:39][OH:40]>[Cl-].[Na+].O.CN(C=O)C>[CH:10]1[C:11]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:39][OH:40])=[O:25])=[O:16])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

6-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acid (335 mg, 1 mmol), triethylamine (151 mg, 1.5 mmol) and 20 ml of DMF were stirred at 0° C. while ethyl chloroformate (163 mg, 1.5 mmol) was added. The mixture was stirred at 0° C. for 2 hours, and then 50% aqueous solution of hydroxylamine (1.32 g, 20 mmol) was added. The mixture was stirred for 3 hours at room temperature, and then diluted with 1000 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (147 mg, 42%) as a yellow solid. 1H NMR (DMSO-d6) δ1.19 (m, 2H, CH2), 1.30 (m, 2H, CH2), 1.48 (m, 2H, CH2), 1.92 (t, J=8.0 Hz, 2H, CH2CO), 3.24 (m, 2H, NCH2), 7.08 (s, 1H, ═CH—CO), 7.28 (m, 2H, Ar—H), 7.41 (m, 2H, Ar—H), 7.76 (m, 1H, Ar—H), 7.81 (m, 2H, Ar—H), 8.53 (t, J=4.0 Hz, 1H, CONH), 8.67 (d, J=8.0 Hz, 1H, Ar—H), 10.32 (s, 1H, NH—O). LC-MS (m/z) 351 (M+1).

Aufarbeitung

additionwas added
stirringThe mixture was stirred for 3 hours at room temperature
filtrationThe solids were collected by vacuum filtration
washwashed with water
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-4e98b7e59e1f4896962dca486b00dd7f
Quelldatensatz: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08178577B2

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