Hydrochloric Acid → HCID 68830468, compound

HRID 747760Notes

Reaction equation

HRID 747760 reaction equation
Cl.[CH2:2]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C@H:26]([NH:37][S:38]([C:41]3[CH:46]=[CH:45][C:44](I)=[CH:43][CH:42]=3)(=[O:40])=[O:39])[CH2:27][O:28][C:29]3[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=3)[C:32]#[N:33])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[CH2:57]([O:64][C:65](C1C=CC=CC=1S(Cl)(=O)=O)=[O:66])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>O1CCOCC1>[CH2:2]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C@H:26]([NH:37][S:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[C:65]([O:64][CH2:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[O:66])(=[O:40])=[O:39])[CH2:27][O:28][C:29]3[CH:36]=[CH:35][CH:34]=[C:31]([C:32]#[N:33])[CH:30]=3)=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 19063854Benzyl 2-(chlorosulfonyl)benzoateHCID 68830378HCID 68830378, compound

Product 1

HCID 68830468HCID 68830468, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5 ml of 4 N hydrogen chloride in dioxane and 2.5 ml of dioxane were added to 500 mg (0.854 mmol) of 3-[(2S)-3-[4-[1-(benzyloxycarbonyl)-4-piperidyloxy]phenyl]-2-(4-iodobenzenesulfonylamino)propoxy]benzonitrile. The mixture was stirred at room temperature for 24 hours, and the solvent was distilled off under reduced pressure, and the resulting residue was dissolved in 8 ml of DMF, and 0.49 ml (2.56 mmol) of di-isopropylethylamine and 398 mg (1.28 mmol) of 2-(benzyloxycarbonyl)benzene sulfonyl chloride were added thereto at 0° C. The mixture was stirred for 1 hour, then allowed to reach room temperature, and stirred for additional 24 hours. The reaction solution was extracted with ethyl acetate, washed with water, 1 N hydrogen chloride and saturated saline, and dried over powdery magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography to obtain the title compound.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. dissolutionthe resulting residue was dissolved in 8 ml of DMF
  3. customat 0° C
  4. stirringThe mixture was stirred for 1 hour
  5. customto reach room temperature
  6. stirringstirred for additional 24 hours
  7. extractionThe reaction solution was extracted with ethyl acetate
  8. washwashed with water, 1 N hydrogen chloride and saturated saline
  9. dry with materialdried over powdery magnesium sulfate
  10. distillationThe solvent was distilled off
  11. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ee5d211d40df42ca845957789211f8fe
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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