Hydrochloric Acid → HCID 68830378, compound

HRID 747758Notes

Reaction equation

HRID 747758 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]C(OC(C)(C)C)=O)[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.[I:54][C:55]1[CH:60]=[CH:59][C:58]([S:61](Cl)(=[O:63])=[O:62])=[CH:57][CH:56]=1>O1CCOCC1.C(OCC)(=O)C>[CH2:2]([O:9][C:10]([N:12]1[CH2:13][CH2:14][CH:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C@H:26]([NH:37][S:61]([C:58]3[CH:59]=[CH:60][C:55]([I:54])=[CH:56][CH:57]=3)(=[O:63])=[O:62])[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)[CH2:16][CH2:17]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73994-Iodobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68829666HCID 68829666, compound

Product 1

HCID 68830378HCID 68830378, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

25 ml of 4 N solution of hydrogen chloride in dioxane and 12.5 ml of dioxane were added to 2.54 g (4.34 mmol) of 3-[(2S)-3-[4-[1-(benzyloxycarbonyl)-4-piperidyloxy]phenyl]-2-(t-butoxycarbonylamino)propoxy]benzonitrile. After stirring at room temperature for 24 hours, the solvent was distilled off under reduced pressure. The residue was dissolved in 40 ml of DMF. 1.77 ml (13.0 mmol) of diisopropylethylamine and 1.97 g (6.51 mmol)) of 4-iodobenzenesulfonyl chloride were added to the solution at 0° C. 30 minutes after, the temperature was elevated to room temperature, and the reaction mixture was stirred for 19 hours. Ater the same isolation process as that of step 1 in Example 1 with ethyl acetate as the extractant, the crude product was obtained, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in 40 ml of DMF
  3. custom30 minutes
  4. customwas elevated to room temperature
  5. stirringthe reaction mixture was stirred for 19 hours
  6. customwhich was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-7064968bbb004e1d82d9ecce9e099775
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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