Diazomethane → HCID 14488066, 화합물

HRID 1614680노트

반응식

HRID 1614680 반응식
[CH3:1][C:2]1[C:7](=[O:8])[O:6][C@H:5]([C@H:9]([C@@H:11]2[C@@:15]3([CH3:34])[CH2:16][CH2:17][C@@:18]45[CH2:24][C@:23]64[CH2:25][CH2:26][C@H:27]([OH:33])[C@:28]([C:30]([OH:32])=[O:31])([CH3:29])[C@@H:22]6[CH2:21][CH2:20][C@H:19]5[C@:14]3([CH3:35])[CH2:13][CH2:12]2)[CH3:10])[CH2:4][CH:3]=1.[N+](=[CH2:38])=[N-]>>[CH3:1][C:2]1[C:7](=[O:8])[O:6][C@H:5]([C@H:9]([C@@H:11]2[C@@:15]3([CH3:34])[CH2:16][CH2:17][C@@:18]45[CH2:24][C@:23]64[CH2:25][CH2:26][C@H:27]([OH:33])[C@:28]([C:30]([O:32][CH3:38])=[O:31])([CH3:29])[C@@H:22]6[CH2:21][CH2:20][C@H:19]5[C@:14]3([CH3:35])[CH2:13][CH2:12]2)[CH3:10])[CH2:4][CH:3]=1

참가 물질

3

반응물 2

HCID 9550DiazomethaneHCID 64510583-Hydroxy-26-oxo-22,26-epoxy-9,19-cyclolanost-24-en-28-oic acid

생성물 1

HCID 14488066HCID 14488066, 화합물

실험 절차

Abrusogenin [10 mg] was methylated in ethereal diazomethane at room temperature overnight. On work-up, abrusogenin methyl ester [8 mg] was obtained as colorless prisms, after recrystallization in EtOAc, and was shown to be pure by tic in solvents 3 (Rf 0.71), 5 (Rf 0.56), and 6 (Rf 0.60). This derivative exhibited the following data: mp 246°-248°; [α]D +31.2° (c 0.08, CHCl3 -MeOH, 1:1); uv, (EtOH) end absorption; ir, νmax (KBr) 3529 (OH), 1710 (C=O), 1258, 1135, 1060, 1018 cm-1, 1H nmr, (360 MHz, CDCl3) δ 6.61 (1H, m, H-24), 4.50 (1H, dd, J=13.4 Hz, J=2.8 Hz, H-22), 4.10 (1H, dd, J=11.3 Hz, J=44 Hz, H-3), 3.71 (3H, s, 29-Ome), 2.57 (1H, m, H-23a), 1.91 (3H, br. s, 27-Me), 1.15 (3H, s, 30-Me), 1.00 (3H, d, J=6.8 Hz, 21-Me), 0.96 (3H, s, 18-Me), 0.93 (3H, s, 28-Me), 0.61, 0.39 (2H, d, J=4.2 Hz, 19-H2) ppm; 13C nmr, (90.8 MHz, CDCl3) δ 177.42 (s, C-29), 166.56 (s, C-26), 139.65 (d, C-24), 128.12 (s, C-25), 80.21 (d, C-22), 75.32 (d, C-3), 54.80 (s, C-4) 51.85 (q, 29-CH3), 48.79 (s, C-14), 47.85 (d, C-8), 47.42 (d, C-17), 45.20 (s, C-13), 44.30 (d, C-5), 40.05 (d, C-20), 35.40 (t, C-12), 32.58 (t, C-15), 31.43 (t, C-1), 29.88 (t, C-19), C-2), 27.85 (t, C-23), 27.55 (t, C-7), 26.32 (t, C-11), 25.52 (t, C-16), 25.04 (s, C-10), 23.07 (t, C-6), 19.91 (s, C-9), 19.38 (q, C-28), 17.86 (q, C-18), 17.14 (q, C-27), 12.82 (q, C-21), 9.26 (q, C-30) ppm; ei-ms, (70 ev) m/z 498 (M+, 1%), 480 (M+ -OH, 3), 465 (1), 448 (4), 421 (1), 367 (3), 314 (22), 299 (6), 247 (11), 215 (14), 199 (11), 173 (30), 147 (42), 133 (55), 119 (60), 111 (68), 107 (76), 105 (68), 95 (100) 81(72), 67 (39), 55 (48).

출처 및 근거

ORD 기록
ord-b217864768b04e6c90f4a48557c53919
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05198427

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