Phenylacetyl chloride → HCID 53672265, compound

HRID 1633286Notes

Reaction equation

HRID 1633286 reaction equation
[NH2:1][C@@H:2]1[C@@H:6]([C:7]([OH:9])=[O:8])[O:5][C@@H:4]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:3]1[OH:28].C(N(CC)CC)C.[C:36]1([CH2:42][C:43](Cl)=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O.O1CCCC1>[C:20]([NH:19][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[C:16]=1[N:17]=[CH:18][N:10]2[C@@H:4]1[O:5][C@H:6]([C:7]([OH:9])=[O:8])[C@@H:2]([NH:1][C:43](=[O:44])[CH2:42][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@H:3]1[OH:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 538540083-amino-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-beta-D-ribofuranuronic acid

Product 1

HCID 53672265HCID 53672265, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronic acid (384 mg) prepared in Example 1 and triethylamine (0.35 ml) in water (10 ml) was dropped a solution of phenylacetyl chloride (0.171 g) in tetrahydrofuran (10 ml) under cooling in an ice bath and stirring, which was continued for 30 minutes at the same temperature. The mixture was evaporated to remove tetrahydrofuran and the remaining aqueous solution was washed with diethyl ether and acidified with 6N hydrochloric acid. The mixture was extracted with a mixture (80 ml) of ethanolchloroform (1:1) and the extract was dried over magnesium sulfate, evaporated and triturated with diethyl ether to give 1-(6-benzoylamino-9H-purin-9-yl)-3-(phenylacetylamino)-1,3-dideoxy-β-D-ribofuranuronic acid (370 mg), mp. 135°-140° C. (dec.).

Workup

  1. temperatureunder cooling in an ice bath
  2. customThe mixture was evaporated
  3. customto remove tetrahydrofuran
  4. washthe remaining aqueous solution was washed with diethyl ether
  5. extractionThe mixture was extracted with a mixture (80 ml) of ethanolchloroform (1:1)
  6. dry with materialthe extract was dried over magnesium sulfate
  7. customevaporated
  8. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-666158718a044b11a23198ddda3ab4e5
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

Loading…