Tetrahydrofuran → (1S)-1-[5-[4-(2-aminoethoxy)-2-methylbenzyl]-2-(benzyloxy)-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol

HRID 1009876ノート

反応式

HRID 1009876 の反応式
O1CCCC1.[CH2:6]([O:13][C@@H:14]1[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:18]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:17]([CH2:36][O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:16][C@H:15]1[C:45]1[CH:50]=[C:49]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][N:61]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:54][C:53]=2[CH3:72])[C:48]([CH3:73])=[CH:47][C:46]=1[O:74][CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.NN.[OH-].[Na+]>CO>[NH2:61][CH2:60][CH2:59][O:58][C:55]1[CH:56]=[CH:57][C:52]([CH2:51][C:49]2[C:48]([CH3:73])=[CH:47][C:46]([O:74][CH2:75][C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)=[C:45]([C@@H:15]3[O:16][C@H:17]([CH2:36][O:37][CH2:38][C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C@@H:18]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C@H:19]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:14]3[O:13][CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:50]=2)=[C:53]([CH3:72])[CH:54]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 86638442HCID 86638442、化合物

生成物 1

HCID 67305276(1S)-1-[5-[4-(2-aminoethoxy)-2-methylbenzyl]-2-(benzyloxy)-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
65 °C

実験手順

To a tetrahydrofuran (0.8 mL) and methanol (0.2 mL) solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)ethoxy]-2-methylbenzyl]-4-methylphenyl]-D-glucitol (60 mg, 0.059 mmol) was added hydrazine monohydrate (30 mg, 0.59 mmol), and the reaction mixture was stirred at 65° C. for an hour. After the mixture was cooled to room temperature, a 2 M aqueous solution of sodium hydroxide was added thereto, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound quantitatively.

後処理

  1. temperatureAfter the mixture was cooled to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-4a38a38369e8410392990e62fc8375db
出典データセット
uspto-grants-2011_07
特許番号
US07973012B2

反応ノート

読み込み中…