Methyl 1-(6-amino-9H-purin-9-yl)-3-[N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyrosylamino]-1,3-dideoxy-beta-D-ribofuranuronate → 3-{2-Amino-3-[4-(carboxymethoxy)phenyl]propanoylamino}-5-(6-aminopurin-9-yl)-4-hydroxyoxolane-2-carboxylic acid

HRID 1633314ノート

反応式

HRID 1633314 の反応式
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:16][C@H:15]([C:17]([O:19]C)=[O:18])[C@@H:14]([NH:21][C:22](=[O:45])[C@H:23]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]([O:43]C)=[O:42])=[CH:35][CH:34]=2)[NH:24]C(OC(C)(C)C)=O)[C@H:12]1[OH:13]>C(O)=O>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:16][C@H:15]([C:17]([OH:19])=[O:18])[C@@H:14]([NH:21][C:22](=[O:45])[C@H:23]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]([OH:43])=[O:42])=[CH:35][CH:34]=2)[NH2:24])[C@H:12]1[OH:13]

参加物

3

反応物 1

HCID 70465257Methyl 1-(6-amino-9H-purin-9-yl)-3-[N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyrosylamino]-1,3-dideoxy-beta-D-ribofuranuronate

生成物 1

HCID 4761393-{2-Amino-3-[4-(carboxymethoxy)phenyl]propanoylamino}-5-(6-aminopurin-9-yl)-4-hydroxyoxolane-2-carboxylic acid収率 78.5%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

A mixture of methyl 1-(6-amino-9H-purin-9-yl)-3-(N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyroylamino)-1,3-dideoxy-β-D-ribofuranuronate (200 mg) prepared in Example 76 and formic acid (3 ml) was stirred for 3 hours at room temperature and evaporated to dryness. To the residue was added 1N aqueous sodium hydroxide to adjust the resulting solution to pH 7 and a further 1N aqueous sodium hydroxide (3 ml) was added thereto. The mixture was stirred for 15 minutes at room temperature and adjusted to pH 2 with 1N hydrochloric acid. The resulting precipitates were filtered, washed with water and dried to give 1-(6-amino-9H-purin-9-yl)-3-(O-carboxymethyl-L-tyrosylamino)-1,3-dideoxy-β-D-ribofuranuronic acid (125 mg), mp. 209°-212° C. (dec.).

後処理

  1. customevaporated to dryness
  2. additionTo the residue was added 1N aqueous sodium hydroxide
  3. additiona further 1N aqueous sodium hydroxide (3 ml) was added
  4. stirringThe mixture was stirred for 15 minutes at room temperature
  5. customThe resulting precipitates
  6. filtrationwere filtered
  7. washwashed with water
  8. customdried

出典と根拠

ORDレコード
ord-3f752606371d424eb9883cd1d5cae6f7
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…