Benzenesulfonyl chloride → 3-[(2S)-2-(benzenesulfonylamino)-3-[4-(1-benzyloxycarbonyl-4-piperidyloxy)phenyl]propoxy]-4-iodobenzonitrile

HRID 747764Notes

Reaction equation

HRID 747764 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([NH:37]C(OC(C)(C)C)=O)[CH2:26][O:27][C:28]3[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=3[I:36])[C:31]#[N:32])=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC(C)C)C(C)C.[C:56]1([S:62](Cl)(=[O:64])=[O:63])[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1.C(OCC)(=O)C>Cl.O1CCOCC1>[C:56]1([S:62]([NH:37][C@@H:25]([CH2:24][C:21]2[CH:20]=[CH:19][C:18]([O:17][CH:14]3[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:10])[CH2:16][CH2:15]3)=[CH:23][CH:22]=2)[CH2:26][O:27][C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=2[I:36])[C:31]#[N:32])(=[O:64])=[O:63])[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 12446309N-Ethyl-2-methyl-N-(2-methylpropyl)propan-1-amineHCID 688341513-[(2S)-3-[4-(1-benzyloxycarbonyl-4-piperidyloxy)phenyl]-2-(t-butoxycarbonylamino)propoxy]-4-iodobenzonitrile

Product 1

HCID 688344743-[(2S)-2-(benzenesulfonylamino)-3-[4-(1-benzyloxycarbonyl-4-piperidyloxy)phenyl]propoxy]-4-iodobenzonitrile

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1.6 g (2.7 mmol) of 3-[(2S)-3-[4-(1-benzyloxycarbonyl-4-piperidyloxy)phenyl]-2-(t-butoxycarbonylamino)propoxy]-4-iodobenzonitrile was dissolved in 4 N solution of hydrogen chloride in dioxane, and the solution was stirred at room temperature overnight. The solvent was distilled off, and the residue was dissolved in dimethylformamide. 1 ml (6 mmol) of N,N-diisobutylethylamine and 0.34 ml (2.7 mmol) of benzenesulfonyl chloride were added to the solution under cooling with ice, and they were stirred for 2 hours. After the isolation process with ethyl acetate as the extractant in the same manner as that of step 1 in Example 1, 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
  2. dissolutionthe residue was dissolved in dimethylformamide
  3. temperatureunder cooling with ice, and they
  4. stirringwere stirred for 2 hours
  5. customwhich was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-81b6a920b1844e3eac0755c9fdff0bac
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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