4-Nitrophenyl chloroformate → HCID 21969273, compound

HRID 2287277Notes

Reaction equation

HRID 2287277 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[Si:14]([O:21][C@@H:22]1[C@@H:26]([CH2:27][OH:28])[O:25][C@@H:24]([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[CH2:23]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C(Cl)Cl.N1C=CC=CC=1>[Si:14]([O:21][C@@H:22]1[C@@H:26]([CH2:27][O:28][C:2]([O:4][C:5]2[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)=[O:3])[O:25][C@@H:24]([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[CH2:23]1)([C:17]([CH3:20])([CH3:18])[CH3:19])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 4538443'-O-(t-butyldimethylsilyl)thymidine

Product 1

HCID 21969273HCID 21969273, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

p-Nitrophenyl chloroformate (252 mg, 1.25 mmol) in anhydrous methylene chloride was added to a stirred solution of 3'-O-(t-butyldimethylsilyl)thymidine (356 mg, 10 mmol, Wang et al. Nucleosides Nucleotides 1998, 17, 1033-1051) in anhydrous methylene chloride (4 mL) and pyridine (0.5 mL). The resulting solution was stirred at room temperature overnight, then cooled with ice, quenched with water (2 mL), stirred at 0° C. for 30 min, diluted with methylene chloride, washed with dilute acetic acid, water, then 5% sodium bicarbonate, dried over sodium sulfate, and concentrated to dryness. Chromatography on silica with ethyl acetate-hexanes (1:1 to 3:2) gave 505 mg of the titled compound as a colorless foam.

Workup

  1. temperaturecooled with ice
  2. customquenched with water (2 mL)
  3. stirringstirred at 0° C. for 30 min
  4. additiondiluted with methylene chloride
  5. washwashed with dilute acetic acid, water
  6. dry with material5% sodium bicarbonate, dried over sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7e25504596b34ff08d30467955c0ac5a
Source dataset
uspto-grants-2000_07
Patent number
US06083482

Reaction notes

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