Trityl chloride → HCID 86651441, compound

HRID 1969312Notes

Reaction equation

HRID 1969312 reaction equation
[C@@H:1]1([N:9]2[CH:13]=[C:12]([C:14]#[C:15][CH3:16])[CH:11]=[C:10]2[CH:17]=[O:18])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.[C:19](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(NC(C)C)(C)C>N1C=CC=CC=1>[C:19]([O:8][CH2:7][C@H:5]1[O:6][C@@H:1]([N:9]2[CH:13]=[C:12]([C:14]#[C:15][CH3:16])[CH:11]=[C:10]2[CH:17]=[O:18])[CH2:2][C@@H:3]1[OH:4])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 7912DiisopropylamineHCID 86651442HCID 86651442, compound

Product 1

HCID 86651441HCID 86651441, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-(2-deoxy-β-D-ribofuranosyl)-4-(1-propynyl)pyrrole-2-carbaldehyde (249 mg, 1.00 mmol) (I. Hirao, et al., Nature Methods, 3: 729-735 (2006)) dissolved in anhydrous pyridine (10 ml) were added trityl chloride (1.18 g, 4.21 mmol) and N,N-diisopropylamine (1.11 ml, 6.40 mmol), and the reaction mixture was stirred at room temperature for 29 hours, and then at 50° C. for 1.5 hours. The reaction solution was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, and the organic layers were washed twice with a saturated aqueous sodium bicarbonate solution and dried over magnesium sulfate. The resulting crude product was purified by column chromatography on silica gel (eluent:dichloromethane:ethyl acetate=100:0→400:3, then dichloromethane:methanol=100:2) to give the title product (395 mg, 80%).

Workup

  1. waitat 50° C. for 1.5 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washthe organic layers were washed twice with a saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. customThe resulting crude product was purified by column chromatography on silica gel (eluent

Sources & evidence

ORD record
ord-316e09a941e24af39783ec1bd69ee265
Source dataset
uspto-grants-2013_04
Patent number
US08426569B2

Reaction notes

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