تفاعل #496802
ord-c9c14704ff6c422294fe040aace22d28
معادلة التفاعل
المتفاعلات
المذيبات
ظروف التفاعل
المعالجة
- 1أخرىPurification by flash chromatography (SiO2, light petroleum:DCM:EtOAc:MeOH, 1:2:1:0.2)
الإجراء التجريبي
The prenylglycine derivative 19 was subjected to the conventional cross metathesis procedure (Section 7.5.4) with cis-2-butene under the following conditions: (2S)-Methyl 2-N-acetylamino-5-methylhex-4-enoate 19 (16.2 mg, 81.4 μmol), DCM (5 mL), 2nd generation Grubbs' catalyst (3.5 mg, 4.1 μmol, 5 mol %), cis-2-butene (5 psi), 50° C., 14 h, 100% conversion into 81. Purification by flash chromatography (SiO2, light petroleum:DCM:EtOAc:MeOH, 1:2:1:0.2) gave (2S)-methyl 2-N-acetylaminohex-4-enoate 81 as a brown oil (12.6 mg, 84%). GC: tR (E/Z)=4.2 min, 4.4 min (GC column 30QC5/BPX5, 150° C. for 1 min, 10° C. min−1 to 280° C. for 6 min). νmax (neat): 3284s, 2966w, 2954m, 2856w, 1747s, 1658s, 1547s, 1437s, 1375s, 1217m, 1142m, 1072w, 1016w, 968m, 848m cm−1. 1H n.m.r. (300 MHz, CDCl3): 1.60 (dd, J=6.3, 1.2 Hz, 3H, H6), 1.95 (s, 3H, CH3CO), 2.36-2.44 (m, 2H, H3), 3.67 (s, 3H, OCH3), 4.55 (dt, J=7.8 Hz, 5.9 Hz, 1H, H2), 5.24 (m, 1H, H5), 5.49 (m, 1H, H4), 6.17 (bd, J=6.4 Hz, 1H, NH). 13C n.m.r. (100 MHz, CDCl3): δ 18.1 (C6), 23.3 (CH3CO), 35.4 (C3), 52.1, 52.4 (C2, OCH3), 124.6, 130.2 (C4, 5), 169.7, 172.6 (C1, CONH). Mass Spectrum (ESI+, MeOH): m/z 208.1 (M+Na)+, C9H15NNaO3 requires 208.1. Spectroscopic data were in agreement with those reported in the literature.117,119