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 1633314노트

반응식

HRID 1633314 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-3f752606371d424eb9883cd1d5cae6f7
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04479942

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