1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-beta-D-ribofuranuronic acid → 1-(6-amino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-1,3-dideoxy-beta-D-ribofuranuronic acid

HRID 1633275Notes

Reaction equation

HRID 1633275 reaction equation
C([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:24][C@H:23]([C:25]([OH:27])=[O:26])[C@@H:22]([NH:28][C:29](=[O:51])[C@H:30]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=2)[NH:31][C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[C@H:20]1[OH:21])(=O)C1C=CC=CC=1>CO.C(N)CCC>[NH2:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:24][C@H:23]([C:25]([OH:27])=[O:26])[C@@H:22]([NH:28][C:29](=[O:51])[C@H:30]([CH2:42][C:43]2[CH:44]=[CH:45][C:46]([O:49][CH3:50])=[CH:47][CH:48]=2)[NH:31][C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[C@H:20]1[OH:21]

Participants

4

Reactant 1

HCID 704659181-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-beta-D-ribofuranuronic acid

Product 1

HCID 704654721-(6-amino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-1,3-dideoxy-beta-D-ribofuranuronic acidYield 78.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8007ButylamineSolvent

Procedure

A suspension of 1-(6-benzoylamino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-1,3-dideoxy-β-D-ribofuranuronic acid (300 mg) prepared in Example 2 in a mixture of methanol (20 ml) and n-butylamine (10 ml) was boiled under reflux for 1 hour. The mixture was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol (7:3). The fractions containing the object compound were combined and the solvent was evaporated to give 1-(6-amino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-1,3-dideoxy-β-D-ribofuranuronic acid (200 mg).

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe mixture was evaporated under reduced pressure
  3. washeluted with a mixture of chloroform and methanol (7:3)
  4. additionThe fractions containing the object compound
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1bb96e1b7f05409a858567e7ebd0710c
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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