Dicyclohexylcarbodiimide → HCID 22828235、化合物

HRID 1633306ノート

反応式

HRID 1633306 の反応式
[CH3:1][O:2][C:3](=[O:21])[C@H:4]1[O:8][C@@H:7]([N:9]2[CH:17]=[N:16][C:15]3[C:10]2=[N:11][CH:12]=[N:13][C:14]=3[NH2:18])[C@H:6]([OH:19])[C@@H:5]1[NH2:20].[C:22]([O:26][C:27]([NH:29][CH:30]([C:39](O)=[O:40])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.O>[NH2:18][C:14]1[N:13]=[CH:12][N:11]=[C:10]2[C:15]=1[N:16]=[CH:17][N:9]2[C@@H:7]1[O:8][C@H:4]([C:3]([O:2][CH3:1])=[O:21])[C@@H:5]([NH:20][C:39](=[O:40])[CH:30]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=2)[NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:28])[C@H:6]1[OH:19]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 41648972-(((Tert-butoxy)carbonyl)amino)-3-(4-chlorophenyl)propanoic acidHCID 54526695HCID 54526695、化合物

生成物 1

HCID 22828235HCID 22828235、化合物収率 35.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of methyl-1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronate (294 mg) prepared in Example 62, N-tert-butoxycarbonyl-β-(4-chlorophenyl)-D,L-alanine (300 mg) and N,N'-dicyclohexylcarbodiimide (206 mg) in tetrahydrofuran (15 ml) and water (5 ml) was stirred overnight. The mixture was diluted with water (50 ml) and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated to dryness. The residue was subjected to column chromatography on silica gel. The elution was carried out with a mixed solvent (chloroform/methanol=97/3). The eluate was evaporated to dryness to give methyl 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-[N-tert-butoxycarbonyl-β-(4-chlorophenyl)-D,L-alanylamino]-β-D-ribofuranuronate (203 mg), mp. 120°-125° C.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customevaporated to dryness
  5. washThe elution
  6. customThe eluate was evaporated to dryness

出典と根拠

ORDレコード
ord-16100e2a11cb4fbab579b8d51d43be9f
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…