Ethyl chloroformate → HCID 68467805, compound

HRID 1698785Notes

Reaction equation

HRID 1698785 reaction equation
CC1(C)[O:9][CH:8]2[CH:4]([CH:5]([CH2:18][OH:19])[O:6][CH:7]2[N:10]2[C:16](=[O:17])[NH:15][C:13](=[O:14])[CH:12]=[CH:11]2)[O:3]1.[CH2:21]([O:23][C:24](Cl)=[O:25])[CH3:22].C(Cl)(Cl)Cl.CO>N1C=CC=CC=1>[CH2:21]([O:23][C:24]([C@@:7]1([N:10]2[CH:11]=[CH:12][C:13](=[O:14])[NH:15][C:16]2=[O:17])[O:6][C@H:5]([CH2:18][OH:19])[C@@H:4]([OH:3])[C@H:8]1[OH:9])=[O:25])[CH3:22]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 351234362-43-6HCID 21584188Chloroform methanol

Product 1

HCID 68467805HCID 68467805, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

To an ice cold solution of 0.5 grams (1.76 millimoles) grams of 2′, 3′-isopropylidene uridine in 10 ml pyridine, 2.64 mmoles (1.5 equivalents) of ethylchloroformate was added dropwise while stirring. The reaction was allowed to warm up to room temperature (25° C.) and stirred overnight (18 hours), at which point TLC (9:1 chloroform/methanol) showed complete conversion of starting material to a single product. The solvent was removed by rotary evaporation under high vacuum, giving a light beige syrup which was carried over into the subsequent deprotection step.

Workup

  1. stirringstirred overnight (18 hours)
  2. customThe solvent was removed by rotary evaporation under high vacuum
  3. customgiving a light beige syrup which

Sources & evidence

ORD record
ord-139fdf35db534fc498806c773ebd749e
Source dataset
uspto-grants-2002_02
Patent number
US06344447B1

Reaction notes

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