Fumaric Acid → HCID 131716951, compound

HRID 1086805Notes

Reaction equation

HRID 1086805 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[OH:9][C@H:10]1[CH2:14][CH2:13][CH2:12][C@@H:11]1[NH:15][C:16]1[C:17]2[N:18]=[CH:19][N:20]([C:30]=2[N:31]=[CH:32][N:33]=1)[C@@H:21]1[O:29][C@H:26]([CH2:27][OH:28])[C@@H:24]([OH:25])[C@H:22]1[OH:23]>C(O)(C)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[OH:9][C@H:10]1[CH2:14][CH2:13][CH2:12][C@@H:11]1[NH:15][C:16]1[C:17]2[N:18]=[CH:19][N:20]([C:30]=2[N:31]=[CH:32][N:33]=1)[C@@H:21]1[O:29][C@H:26]([CH2:27][OH:28])[C@@H:24]([OH:25])[C@H:22]1[OH:23]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 9884817N-((1S,trans)-2-hydroxycyclopentyl)adenosine

Product 1

HCID 131716951HCID 131716951, compoundYield 134.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Fumaric acid (1.2 g) was added to a refluxing solution of N-[(1S,trans)-2-hydroxycyclopentyl]adenosine (7.03 g) in isopropanol (105 ml). The resulting hot solution was filtered, and the filtrate was cooled and allowed to crystallise. After 2 h at 20° the crystalline product was isolated by filtration, washed with isopropanol (10 ml) and dried in vacuo at 50° for 20 h to give the title compound (6.5 g), m.p. 179°-180°. The chromatographic behaviour of this salt resembled that of an authentic sample of the free base.

Workup

  1. filtrationThe resulting hot solution was filtered
  2. temperaturethe filtrate was cooled
  3. customto crystallise
  4. customAfter 2 h at 20° the crystalline product was isolated by filtration
  5. washwashed with isopropanol (10 ml)
  6. customdried in vacuo at 50° for 20 h

Sources & evidence

ORD record
ord-5f5596ff915f4958b6821edfc51b76c1
Source dataset
uspto-grants-1991_07
Patent number
US05032583

Reaction notes

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