HCID 70466244, compound → 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-amino-beta-D-ribofuranuronic acid monohydrate

HRID 1633320Notes

Reaction equation

HRID 1633320 reaction equation
O.Cl.Cl.[NH2:4][C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[C@@H:14]1[O:19][C@H:18]([C:20]([OH:22])=[O:21])[C@@H:17]([NH:23]C(=O)[C@H](CC2C=CC(OC)=CC=2)N)[C@H:15]1[OH:16]>[OH-].[Na+]>[OH2:16].[NH2:4][C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[C@@H:14]1[O:19][C@H:18]([C:20]([OH:22])=[O:21])[C@@H:17]([NH2:23])[C@H:15]1[OH:16]

Participants

3

Reactant 1

HCID 70466244HCID 70466244, compound

Product 1

HCID 704655221-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-amino-beta-D-ribofuranuronic acid monohydrateYield 165.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-(O-methyl-L-tyrosylamino)-β-D-ribofuranuronic acid dihydrochloride monohydrate (5.48 g) prepared in Example 98 in 1N methanolic sodium hydroxide solution (1000 ml) was heated under reflux for 20 hours. The reaction mixture was evaporated and the residue was neutralized with concentrated hydrochloric acid. The aqueous solution was subjected to column chromatography on a non-ionic adsorption resin "HP-20" (trade mark, Mitsubishi Chemical Industries Ltd.) (500 ml). The elution was carried out with water, and the eluate was concentrated, stood overnight. The resulting precipitates were collected, washed with water, and dried to give 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronic acid monohydrate (2.47 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. customThe reaction mixture was evaporated
  4. washThe elution
  5. concentrationthe eluate was concentrated
  6. customThe resulting precipitates
  7. customwere collected
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-64d413c61d0145bd8e58f9b00d9a451f
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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