Phenylacetyl chloride → HCID 53672265、化合物

HRID 1633286ノート

反応式

HRID 1633286 の反応式
[NH2:1][C@@H:2]1[C@@H:6]([C:7]([OH:9])=[O:8])[O:5][C@@H:4]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:3]1[OH:28].C(N(CC)CC)C.[C:36]1([CH2:42][C:43](Cl)=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O.O1CCCC1>[C:20]([NH:19][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[C:16]=1[N:17]=[CH:18][N:10]2[C@@H:4]1[O:5][C@H:6]([C:7]([OH:9])=[O:8])[C@@H:2]([NH:1][C:43](=[O:44])[CH2:42][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@H:3]1[OH:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

6

反応物 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 538540083-amino-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-beta-D-ribofuranuronic acid

生成物 1

HCID 53672265HCID 53672265、化合物収率 73.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronic acid (384 mg) prepared in Example 1 and triethylamine (0.35 ml) in water (10 ml) was dropped a solution of phenylacetyl chloride (0.171 g) in tetrahydrofuran (10 ml) under cooling in an ice bath and stirring, which was continued for 30 minutes at the same temperature. The mixture was evaporated to remove tetrahydrofuran and the remaining aqueous solution was washed with diethyl ether and acidified with 6N hydrochloric acid. The mixture was extracted with a mixture (80 ml) of ethanolchloroform (1:1) and the extract was dried over magnesium sulfate, evaporated and triturated with diethyl ether to give 1-(6-benzoylamino-9H-purin-9-yl)-3-(phenylacetylamino)-1,3-dideoxy-β-D-ribofuranuronic acid (370 mg), mp. 135°-140° C. (dec.).

後処理

  1. temperatureunder cooling in an ice bath
  2. customThe mixture was evaporated
  3. customto remove tetrahydrofuran
  4. washthe remaining aqueous solution was washed with diethyl ether
  5. extractionThe mixture was extracted with a mixture (80 ml) of ethanolchloroform (1:1)
  6. dry with materialthe extract was dried over magnesium sulfate
  7. customevaporated
  8. customtriturated with diethyl ether

出典と根拠

ORDレコード
ord-666158718a044b11a23198ddda3ab4e5
出典データセット
uspto-grants-1984_10
特許番号
US04479942

反応ノート

読み込み中…