HCID 69742071, compound → HCID 131724820, compound

HRID 1814215Notes

Reaction equation

HRID 1814215 reaction equation
COC1C=CC(C([C@@:22]2([OH:61])[C@@H:26]([CH2:27][O:28][C:29]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)(C3C=CC(OC)=CC=3)[C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[O:25][C@@H:24]([N:52]3[CH:60]=[C:58]([CH3:59])[C:56](=[O:57])[NH:55][C:53]3=[O:54])[CH2:23]2)(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1>C(#N)C.O>[CH2:47]([CH2:46][C:29]([O:61][C@@H:22]1[C@@H:26]([CH2:27][O:28][C:29]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)([C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)[C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)[O:25][C@@H:24]([N:52]2[CH:60]=[C:58]([CH3:59])[C:56](=[O:57])[NH:55][C:53]2=[O:54])[CH2:23]1)=[O:28])[CH2:48][CH2:49][CH3:50]

Participants

3

Reactant 1

HCID 69742071HCID 69742071, compound

Product 1

HCID 131724820HCID 131724820, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a stirred solution of 40.0 g of thymidine (0.165 mol) in 500 mL of pyridine was added 56.0 g of dimethoxytrityl chloride (0.165 mol), and the mixture was stirred at room temperature for 3 hours. To the mixture, 16.7 g of sodium hydrogen carbonate was added. The resulting mixture was stirred at room temperature for 30 min and evaporated under a reduced pressure. To the residue was added 500 mL of n-butyl acetate. To the stirred mixture was added 500 mL of water and the mixture was stirred for 10 min. Then, the organic layer was separated and washed with 500 mL of water. The organic layer was evaporated under a reduced pressure. The residue was recrystallized from 900 mL of n-butyl acetate to give a crystalline product, which was then collected by filtration. The crystalline product was dried in vacuo at 50° C. to a constant weight to give 74.6 g of the product. The product was analyzed by high performance chromatography (HPLC) with a reverse-phase octadecyl silica gel column using a mixture of acetonitrile/water (75/25) as an eluent and using a UV detector (254 nm), indicating a purity of 99.6%. A major impurity was 3′,5′-O-bis(4,4′-dimethoxytrityl)thymidine with an HPLC peak area of 0.3%. An yield was 75%.

Sources & evidence

ORD record
ord-fc8307b6be294019b747cbff2a1fa48c
Source dataset
uspto-grants-2005_04
Patent number
US06875860B2

Reaction notes

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