Carbon Dioxide → HCID 178521060, compound

HRID 1764747Notes

Reaction equation

HRID 1764747 reaction equation
[BH4-].[Na+].[Na].C(=O)=O.[C@@H:7]1([N:15]2[C:19]3[N:20]=[CH:21][NH:22][CH2:23][C@@H:24]([OH:25])[C:18]=3[N:17]=[CH:16]2)[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[CH2:8]1>C(O)C>[C@H:7]1([N:15]2[C:19]3[N:20]=[CH:21][NH:22][CH2:23][C@@H:24]([OH:25])[C:18]=3[N:17]=[CH:16]2)[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[CH2:8]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 4311764Sodium borohydrideHCID 5360545SodiumHCID 178521059HCID 178521059, compound

Product 1

HCID 178521060HCID 178521060, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 25 mg. of 6,7-dihydro-3-[3,5-di-O-(p-toluoyl)-60 ,β-D-erythro-pentofuranosyl]imidazo[4,5-d][1,3]diazepin-8(3H)-one in 5 ml. of ethanol is treated with 10 mg. of sodium borohydride and stirred at room temperature for 15 minutes. About 5 mg. of sodium is then added, the solution is stirred at room temperature for 15 minutes, then neutralized with carbon dioxide. The mixture is evaporated at reduced pressure and the residue is partitioned between 10 ml. of ether and 10 ml. of water. The aqueous phase is separated and evaporated at reduced pressure. The residue is applied to the top of a 1 × 10 cm. column of Dowex 50×2 resin (a strongly acidic cation exchange resin) in the ammonium form. The resin is eluted with 25 ml. of 0.01N aqueous ammonia and the eluate is evaporated at reduced pressure to give a residue consisting of a mixture of the four possible isomers, one of which is (R)-3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (pentostatin).

Workup

  1. customThe mixture is evaporated at reduced pressure
  2. customthe residue is partitioned between 10 ml
  3. customThe aqueous phase is separated
  4. customevaporated at reduced pressure
  5. washThe resin is eluted with 25 ml
  6. customof 0.01N aqueous ammonia and the eluate is evaporated at reduced pressure
  7. customto give a residue
  8. additionconsisting of a mixture of the four possible isomers, one of which

Sources & evidence

ORD record
ord-8d75c73ada2d4a4eb92cda41d21fbcc5
Source dataset
uspto-grants-1978_09
Patent number
US04117229

Reaction notes

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