Ethanol → HCID 10389014, compound

HRID 623249Notes

Reaction equation

HRID 623249 reaction equation
[O:1]([CH2:8][CH:9]1[O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:12][C:13]1[N:14]([C:24]2[N:25]=[CH:26][N:27]=[C:28]([NH2:31])[C:29]=2[N:30]=1)[C@@H:15]1[O:23][C@H:20]([CH2:21][OH:22])[C@@H:18]([OH:19])[C@H:16]1[OH:17].C(O)C>N1C(C)=CC=CC=1C.C(OC(=O)C)C.C(O)C>[OH:11][CH:9]([CH2:8][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][S:12][C:13]1[N:14]([C:24]2[N:25]=[CH:26][N:27]=[C:28]([NH2:31])[C:29]=2[N:30]=1)[C@@H:15]1[O:23][C@H:20]([CH2:21][OH:22])[C@@H:18]([OH:19])[C@H:16]1[OH:17]

Participants

6

Reactant 3

HCID 702EthanolHCID 31217Phenyl glycidyl etherHCID 178508659HCID 178508659, compound

Product 1

HCID 10389014HCID 10389014, compound

Reagents, catalysts & solvents 2

HCID 79372,6-LutidineCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of 1-phenoxy-2,3-epoxypropane (7.3 g, 48.6 mmoles), 8-mercaptoadenosine (11.5 g, 38.4 mmoles), 2,6 lutidine (about 20 drops) and ethanol (300 ml) is heated at reflux temperature for 1 hour, then it is concentrated to a small volume and ethyl ether is added to precipitate the compound of the title as a raw product. The precipitate is recovered by filtration, washed with ether and dried, dissolved in boiling ethanol, added to an equal amount (by weight) of silica gel and concentrated to dryness. The obtained residue is charged on a silica gel (120 g) column prepared in ethyl acetate and developed with an ethylacetate/ethanol 9/1 mixture. Fractions, containing only the end product, are combined and crystallized from dichloroethane/ethanol 9/1 yielding 6.5 g of the compound of the title. M.p. 100°-110° C. Fusion endotherm at 105° C. in DSC and [α]D30 -48.23° (c=1, CH3OH).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 1 hour
  3. concentrationit is concentrated to a small volume and ethyl ether
  4. additionis added
  5. customto precipitate the compound of the title as a raw product
  6. filtrationThe precipitate is recovered by filtration
  7. washwashed with ether
  8. customdried
  9. dissolutiondissolved
  10. additionadded to an equal amount (by weight) of silica gel
  11. concentrationconcentrated to dryness
  12. additionThe obtained residue is charged on a silica gel (120 g) column
  13. customprepared in ethyl acetate
  14. additionFractions, containing only the end product
  15. customcrystallized from dichloroethane/ethanol 9/1 yielding 6.5 g of the compound of the title
  16. customat 105° C.

Sources & evidence

ORD record
ord-efc12a05ed544864a56971ed61026b57
Source dataset
uspto-grants-1988_09
Patent number
US04774325

Reaction notes

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