Pyridine → HCID 86696316, compound

HRID 882390Notes

Reaction equation

HRID 882390 reaction equation
[P:1]([O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].N1C=CC=CC=1.Cl[C:39]([O:41][CH:42]([Cl:44])[CH3:43])=[O:40]>C(Cl)Cl>[Cl:44][CH:42]([O:41][C:39](=[O:40])[O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][P:1]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH3:43]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5213051-Chloroethyl chloroformateHCID 86696313HCID 86696313, compound

Product 1

HCID 86696316HCID 86696316, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of dibenzyl 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl phosphate (500 mg, 1.1 mmol) and pyridine (200 mg, 205 μl, 2.53 mmol) in methylene chloride (6 mL) at −78° C. was added slowly 1-chloroethyl chloroformate (178 mg, 134 μl, 1.24 mmol) in methylene chloride (2 mL). After addition, the reaction mixture was allowed to stir at −78° C. for 1.5 h. Then the cold bath was removed and the reaction mixture was warmed up to room temperature. 1H-NMR showed the completion of the reaction. The reaction mixture was concentrated in vacuo. The residue was reconstituted with diethyl ether. The solids in the ethereal solution were filtered off and washed thoroughly with diethyl ether. The filtrate and washing solutions were combined and concentrated to give carbonic acid 2-(2-{2-[2-(bis-benzyloxy-phosphoryloxy)-ethoxy]-ethoxy}-ethoxy)-ethyl ester 1-chloro-ethyl ester as clear light-yellow thick oil. The crude product was used without further purification.

Workup

  1. additionAfter addition
  2. customThen the cold bath was removed
  3. temperaturethe reaction mixture was warmed up to room temperature
  4. customthe completion of the reaction
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. filtrationThe solids in the ethereal solution were filtered off
  7. washwashed thoroughly with diethyl ether
  8. washThe filtrate and washing solutions
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1da09e21b98a4a3596ac87c7fe8d2e57
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

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