Triethylamine → HCID 22674975, compound

HRID 1005768Notes

Reaction equation

HRID 1005768 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([OH:10])=O)[CH2:3][CH2:2]1.C(N(CC)CC)C.C([Cl:23])(=O)OCC.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2/[CH:42]=[CH:43]/[C:44]2[CH:49]=[CH:48][N+:47]([O-:50])=[CH:46][CH:45]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(Cl)Cl.CO>[ClH:23].[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][C:8]([N:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2/[CH:42]=[CH:43]/[C:44]2[CH:45]=[CH:46][N+:47]([O-:50])=[CH:48][CH:49]=2)[S:32]([C:29]2[CH:28]=[CH:27][C:26]([O:25][CH3:24])=[CH:31][CH:30]=2)(=[O:33])=[O:34])=[O:10])[CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4389684-Morpholineacetic acidHCID 178492875HCID 178492875, compound

Product 1

HCID 22674975HCID 22674975, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Morpholinoacetic acid (5.18 g) prepared in the same manner as Reference Example 1 was dissolved in methylene chloride (230 ml), and triethylamine (4.86 g) was added thereto. To the mixture was added dropwise ethyl chlorocarbonate (5.21 g) under ice-cooling, and the mixture was stirred for thirty minutes at room temperature. To the mixture was added (E)-4-(2-(2-(N-(4-methoxybenzenesulfonyl)amino)phenyl)ethenyl)pyridine 1-oxide (7.65 g) and the mixture was further stirred for three hours at room temperature. The reaction solution was washed with water, dried over magnesium sulfate and concentrated. The resultant residue was dissolved in acetonitrile. To the solutuion was added hydrochloric acid-methanol and the mixture was stirred over night at room temperature. The precipitated crystals were filtered off, washed with acetonitrile and further with ether and the crude crystals were obtained. The recrystallizaion from methanol yielded the objective compound (8.16 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for three hours at room temperature
  3. washThe reaction solution was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. dissolutionThe resultant residue was dissolved in acetonitrile
  7. additionTo the solutuion was added hydrochloric acid-methanol
  8. stirringthe mixture was stirred over night at room temperature
  9. filtrationThe precipitated crystals were filtered off
  10. washwashed with acetonitrile and further with ether
  11. customthe crude crystals were obtained

Sources & evidence

ORD record
ord-0780f9d6e9b04eabbe6cf18af2a97bc7
Source dataset
uspto-grants-2004_09
Patent number
US06787546B2

Reaction notes

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