Tacrolimus → 1,14-Dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-propyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

HRID 55104

反応式

HRID 55104 の反応式
[CH3:1][C@H:2]1[CH2:33][C:32]([CH3:34])=[CH:31][C@@H:30]([CH2:35][CH:36]=[CH2:37])[C:28](=[O:29])[CH2:27][C@H:26]([OH:38])[C@@H:25]([CH3:39])[C@@H:24](/[C:40](/[CH3:51])=[CH:41]/[C@H:42]2[CH2:47][C@@H:46]([O:48][CH3:49])[C@H:45]([OH:50])[CH2:44][CH2:43]2)[O:23][C:21](=[O:22])[C@H:20]2[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]2)[C:13](=[O:14])[C:11](=[O:12])[C@:9]2([OH:52])[O:10][C@@H:5]([C@@H:6]([O:54][CH3:55])[CH2:7][C@H:8]2[CH3:53])[C@@H:4]([O:56][CH3:57])[CH2:3]1>C(OCC)(=O)C.[Pd]>[OH:52][C:9]12[O:10][CH:5]([CH:6]([O:54][CH3:55])[CH2:7][CH:8]1[CH3:53])[CH:4]([O:56][CH3:57])[CH2:3][CH:2]([CH3:1])[CH2:33][C:32]([CH3:34])=[CH:31][CH:30]([CH2:35][CH2:36][CH3:37])[C:28](=[O:29])[CH2:27][CH:26]([OH:38])[CH:25]([CH3:39])[CH:24]([C:40]([CH3:51])=[CH:41][CH:42]1[CH2:43][CH2:44][CH:45]([OH:50])[CH:46]([O:48][CH3:49])[CH2:47]1)[O:23][C:21](=[O:22])[CH:20]1[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]1)[C:13](=[O:14])[C:11]2=[O:12]

参加物

4

反応物 1

HCID 445643Tacrolimus

生成物 1

HCID 571132511,14-Dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-propyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of the FR-900506 substance (50 mg) in ethyl acetate (2 ml) was subjected to catalytic reduction using 10% palladium on carbon (10 mg) under atmospheric pressure at room temperature for 20 minutes. The reaction mixture was filtered and the filtrate was evaporated to dryness, which was purified on thin layer chromatography. Development with a mixture of chloroform and acetone (5:1 v/v) gave 1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-propyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (50.0 mg).

後処理

  1. customat room temperature
  2. customfor 20 minutes
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated to dryness, which
  5. customwas purified on thin layer chromatography
  6. additionDevelopment with a mixture of chloroform and acetone (5:1 v/v)

出典と根拠

ORDレコード
ord-c43d37d4ab25430ea013783c1f049613
出典データセット
uspto-grants-1997_04
特許番号
US05624842

関連ノート

読み込み中…