HCID 86651443, compound → HCID 58165899, compound

HRID 1969314Notes

Reaction equation

HRID 1969314 reaction equation
C([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:31]=[C:30]([C:32]#[C:33][CH3:34])[CH:29]=[C:28]2[CH:35]=[O:36])[CH2:24][CH2:23]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(O)(=O)C>[C@@H:25]1([N:27]2[CH:31]=[C:30]([C:32]#[C:33][CH3:34])[CH:29]=[C:28]2[CH:35]=[O:36])[O:26][C@H:22]([CH2:21][OH:20])[CH2:23][CH2:24]1

Participants

3

Reactant 1

HCID 86651443HCID 86651443, compound

Product 1

HCID 58165899HCID 58165899, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(2,3-dideoxy-5-O-trityl-β-D-ribofuranosyl)-4-(1-propynyl)pyrrole-2-carbaldehyde (82 mg, 171 μmol) dissolved in 80% acetic acid (10 ml) was stirred at room temperature for 3 hours, and then at 50° C. for 2 hours. The reaction solution was concentrated under reduced pressure and repeated co-evaporation with water. The resulting crude product was purified by column chromatography on silica gel (0-1% CH3OH in CH2Cl2) and RP-HPLC (35-80% CH3CN in water, 12 min) to give the title product (31 mg, 78%).

Workup

  1. waitat 50° C. for 2 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customThe resulting crude product was purified by column chromatography on silica gel (0-1% CH3OH in CH2Cl2) and RP-HPLC (35-80% CH3CN in water, 12 min)

Sources & evidence

ORD record
ord-d904a232f4be4526a58c83dcde855c0b
Source dataset
uspto-grants-2013_04
Patent number
US08426569B2

Reaction notes

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