Butylamine → 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-L-phenylalanylamino)-beta-D-ribofuranuronic acid

HRID 1633291Notes

Reaction equation

HRID 1633291 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:49])[C@H:30]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[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.C(N)CCC>CO>[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:49])[C@H:30]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[NH:31][C:32]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:33])[C@H:20]1[OH:21]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 228282251-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-L-phenylalanylamino)-beta-D-ribofuranuronic acid

Product 1

HCID 704656061-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-L-phenylalanylamino)-beta-D-ribofuranuronic acidYield 73.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(6-benzoylamino-9H-purin-9yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-L-phenylalanylamino)-β-D-ribofuranuronic acid (432 mg) prepared in Example 5 and n-butylamine (3.5 ml) in methanol (15 ml) was refluxed for 50 minutes and evaporated to dryness. The residue was dissolved in a mixture of water and diethyl ether and the aqueous layer was separated out. The aqueous solution was adjusted to pH 4 to 5 with 10% hydrochloric acid and the resulting precipitates were collected by filtration, washed with water and dried to give 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-L-phenylalanylamino)-β-D-ribofuranuronic acid (267 mg), mp. 195°-201° C. (dec.).

Workup

  1. temperaturewas refluxed for 50 minutes
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in a mixture of water and diethyl ether
  4. customthe aqueous layer was separated out
  5. customthe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-d5095f1dd54a475da6fdab3030e87c2d
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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