HCID 88636778, compound → HCID 22839978, compound

HRID 623250Notes

Reaction equation

HRID 623250 reaction equation
[SH:1][C:2]1[N:3]([C:13]2[N:14]=[CH:15][N:16]=[C:17]([NH2:20])[C:18]=2[N:19]=1)[C@@H:4]1[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]1[OH:6].[CH3:21][CH2:22][CH2:23][CH:24]([O:33][C:34]([C:36]1([CH:46]=[CH:45][CH:44]=[CH:43][CH2:42]1)OCC1OC1)=[O:35])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>N1C(C)=CC=CC=1C.C(O)C>[OH:6][CH:5]([CH2:4][O:12][C:46]1[CH:45]=[CH:44][CH:43]=[CH:42][C:36]=1[C:34]([O:33][CH:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:23][CH2:22][CH3:21])=[O:35])[CH2:7][S:1][C:2]1[N:3]([C:13]2[N:14]=[CH:15][N:16]=[C:17]([NH2:20])[C:18]=2[N:19]=1)[C@@H:4]1[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]1[OH:6]

Participants

5

Reactant 2

HCID 88636778HCID 88636778, compoundHCID 178508659HCID 178508659, compound

Product 1

HCID 22839978HCID 22839978, compoundYield 114.2%

Reagents, catalysts & solvents 2

HCID 79372,6-LutidineCatalystHCID 702EthanolSolvent

Procedure

A suspension of 8-mercapto-adenosine (4.9 g, 16.4 mmole), 1-(4-dodecyloxycarbonyl)phenoxy-2,3-epoxy-propane (5.4 g, 14,9 mmole), 2,6-lutidine (5 drops) and absolute ethanol (100 ml) is heated at reflux temperature for a couple of hours, then the obtained solution is allowed to cool slowly under stirring. The white crystalline precipitate which forms is recovered by filtration, washed with ethanol (about 25 ml) and dried under vacuum yielding 6.2 g of the compound of the title with m.p. 163°-65° C.; [α]D20 -39.98° (c=1 in dimethylformamide).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for a couple of hours
  3. temperatureto cool slowly
  4. filtrationThe white crystalline precipitate which forms is recovered by filtration
  5. washwashed with ethanol (about 25 ml)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-3aaf33bc5a5d40f8afa7722dc68a3499
Source dataset
uspto-grants-1988_09
Patent number
US04774325

Reaction notes

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