Morpholine → (1S,3'R,4'S,5'S,6'R)-5-chloro-6-(4-ethylbenzyl)-6'-(morpholinomethyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triol

HRID 1716967ノート

反応式

HRID 1716967 の反応式
CC1C=CC(S(O[CH2:12][C@H:13]2[O:18][C@@:17]3([C:26]4[C:21](=[CH:22][C:23]([Cl:36])=[C:24]([CH2:27][C:28]5[CH:33]=[CH:32][C:31]([CH2:34][CH3:35])=[CH:30][CH:29]=5)[CH:25]=4)[CH2:20][O:19]3)[C@H:16]([OH:37])[C@@H:15]([OH:38])[C@@H:14]2[OH:39])(=O)=O)=CC=1.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>>[Cl:36][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][C:24]=1[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][CH3:35])=[CH:32][CH:33]=1)[C@:17]1([C@H:16]([OH:37])[C@@H:15]([OH:38])[C@H:14]([OH:39])[C@@H:13]([CH2:12][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[O:18]1)[O:19][CH2:20]2

参加物

3

反応物 2

HCID 8083MorpholineHCID 59013460((1S,3'R,4'S,5'S,6'R)-5-chloro-6-(4-ethylbenzyl)-3',4',5'-trihydroxy-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-6'-yl)methyl 4-methylbenzenesulfonate

生成物 1

HCID 59013464(1S,3'R,4'S,5'S,6'R)-5-chloro-6-(4-ethylbenzyl)-6'-(morpholinomethyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triol

実験手順

((1S,3′R,4′S,5′S,6′R)-5-chloro-6-(4-ethylbenzyl)-3′,4′,5′-trihydroxy-3′,4′,5′,6′-tetrahydro-3H-spiro[isobenzofuran-1,2′-pyran]-6′-yl)methyl 4-methylbenzenesulfonate (20 mg, 0.034 mmol) was dissolved in 1 mL of morpholine. Then the solution was allowed to reflux overnight. Concentration under reduced pressure provided the crude product, which was purified by preparative TLC to give 15 mg of title compound. 1H NMR (CD3OD, 400 MHz) δ 7.37 (s, 1H), 7.18 (s, 1H), 7.11 (d, J=8.0 Hz, 2H), 7.09 (d, J=8.8 Hz, 2H), 5.17 (d, J=13.2 Hz, 1H), 5.11 (d, J=13.2 Hz, 1H), 4.65-4.60 (m, 2H), 4.18-4.00 (m, 4H), 3.82-3.50 (m, 7H), 3.31-3.25 (m, 1H), 3.08-2.99 (m, 2H), 2.61 (q, J=7.6 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H); MS ESI (m/z) 490 (M+1)+, calc. 489.

後処理

  1. temperatureto reflux overnight
  2. concentrationConcentration under reduced pressure
  3. customprovided the crude product, which
  4. customwas purified by preparative TLC

出典と根拠

ORDレコード
ord-40263ae52315448cafee47630e09d8f3
出典データセット
uspto-grants-2010_09
特許番号
US07803778B2

反応ノート

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