Chlorosuccinimide → (Chloro(phenylmethoxy)phosphoryl)oxymethylbenzene

HRID 1597132Notes

Reaction equation

HRID 1597132 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([O:16][P:17]([O-:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1C=CC=CC=1>[P:17]([Cl:1])([O:16][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:26]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 21904359Dibenzylphosphite

Product 1

HCID 4641201(Chloro(phenylmethoxy)phosphoryl)oxymethylbenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
40 °C

Procedure

Dibenzyl chlorophosphate was prepared by adding N-chlorosuccinimide (1.28 g) to a stirred solution of dibenzylphosphite (2.5 g) in benzene (100 ml) at room temperate. After 2 hrs at room temperature the solid (succinimide) was filtered off and the filtrate concentrated to about 5 ml, which was added dropwise to a solution of phenyl 2,3,4-tri-O-acetyl-D-mannoside (3.3 g) in dry pyridine (15 ml) at 0° C. with sting over 1 hour and the mixture allowed to stand at room temperature over night. The mixture was then heated at 40° C. for 2 hours. The solvent was evaporated off under reduced pressure and the residue chromatographed on a silica gel column (silica gel 60; 2.5×50 cm). Initial fractions eluted with methylene chloride were discarded and subsequent elution with ehloroform gave phenyl 2,3,4-tri-O-acetyl-D-mannoside 6-dibenzylphosphate (2.6 g). Calculated for C32H35O12P.2H2O; C, 56.6%; H, 5.8%. Found: C, 56.7%; H, 5.8%.

Workup

  1. filtrationAfter 2 hrs at room temperature the solid (succinimide) was filtered off
  2. concentrationthe filtrate concentrated to about 5 ml, which
  3. additionwas added dropwise to a solution of phenyl 2,3,4-tri-O-acetyl-D-mannoside (3.3 g) in dry pyridine (15 ml) at 0° C.
  4. waitto stand at room temperature over night
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe residue chromatographed on a silica gel column (silica gel 60; 2.5×50 cm)
  7. washInitial fractions eluted with methylene chloride
  8. washsubsequent elution with ehloroform

Sources & evidence

ORD record
ord-5bc6dc8cca734653832a89448721aac9
Source dataset
uspto-grants-2001_09
Patent number
US06294521B1

Reaction notes

Loading…