Triethylamine → HCID 22557758, compound

HRID 984064Notes

Reaction equation

HRID 984064 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].CN(C1C=CC=CN=1)C.C(N(CC)CC)C>C(Cl)Cl>[C:1]([OH:4])(=[O:3])[CH3:2].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[S:20]([CH3:23])(=[O:22])=[O:21])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 218852-DimethylaminopyridineHCID 22557731HCID 22557731, compound

Product 1

HCID 22557758HCID 22557758, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g (0.003 mol) of 4-benzyloxy-3-(methansulfonylamino)benzene acetate (WO 96/04233) in 20 ml of methylene chloride, 0.50 ml (0.0033 mol) of 95% benzyl chloroformate, 0.006 g of dimethylaminopyridine and 0.46 ml (0.0033 mol) of triethylamine is stirred at 50° C. for 10 hours. The solvent is evaporated, the residue is taken up in methylene chloride, washing with water is carried out, the two phases are separated, the organic phase is dried over sodium sulfate and filtered, and the solvent is evaporated under reduced pressure. Purification is carried out by chromatography on a column of silica gel, elution being carried out with ethyl acetate. The title compound is obtained.

Workup

  1. customThe solvent is evaporated
  2. washwashing with water
  3. customthe two phases are separated
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent is evaporated under reduced pressure
  7. customPurification
  8. washis carried out by chromatography on a column of silica gel, elution

Sources & evidence

ORD record
ord-e035e404c6e1475fbd36a0ccb226951b
Source dataset
uspto-grants-2005_03
Patent number
US06867220B2

Reaction notes

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