Hydrochloric Acid → HCID 70466244, compound

HRID 1633276Notes

Reaction equation

HRID 1633276 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]([OH:19])=[O:18])[C@@H:14]([NH:20][C:21](=[O:43])[C@H:22]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)[NH:23]C(OCC2C=CC=CC=2)=O)[C@H:12]1[OH:13].[ClH:44]>O.[Pd]>[OH2:13].[ClH:44].[ClH:44].[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:20][C:21](=[O:43])[C@H:22]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)[NH2:23])[C@H:12]1[OH:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 704654721-(6-amino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-1,3-dideoxy-beta-D-ribofuranuronic acid

Product 1

HCID 70466244HCID 70466244, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A suspension of 1-(6-amino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-1,3-dideoxy-β-D-ribofuranuronic acid (150 mg) prepared in Example 3 in water (200 ml) was adjusted to pH 3 with 1N hydrochloric acid. The resulting mixture was hydrogenated under medium pressure (3.0-3.5 atm.) over palladium black (30 mg) for 3 hours. The catalyst was removed by filtration and the filtrate was adjusted to pH 7 with 1N sodium hydroxide. The resulting mixture was concentrated under reduced pressure to a volume of 30 ml. The concentrate was applied to a column of non ionic adsorption resin "HP-20" (trade mark, Mitsubishi Chemical Industries, Ltd.) (50 ml) and the column was washed with water (100 ml) and then eluted with a mixture of methanol and water (3:7)(100 ml). The solvent was evaporated under reduced pressure and the residue was crystallized from 0.1N hydrochloric acid to give 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-(O-methyl-L-tyrosylamino)-β-D-ribofuranuronic acid dihydrochloride monohydrate (60 mg), mp. 215°-230° C. (dec.).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationThe resulting mixture was concentrated under reduced pressure to a volume of 30 ml
  3. washthe column was washed with water (100 ml)
  4. washeluted with a mixture of methanol and water (3:7)(100 ml)
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was crystallized from 0.1N hydrochloric acid

Sources & evidence

ORD record
ord-361d679b686b41e882e0eb9ae53c608c
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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