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 1633314Notes

Reaction equation

HRID 1633314 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-3f752606371d424eb9883cd1d5cae6f7
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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