Tetrahydrofuran → HCID 18727253, compound

HRID 1856895Notes

Reaction equation

HRID 1856895 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[CH2:24]([O:31][NH:32][C:33]([C@H:35]1[CH2:40][N:39]([S:41]([N:44]([CH3:46])[CH3:45])(=[O:43])=[O:42])[CH2:38][CH2:37][N:36]1[S:47]([N:50]1[CH2:55][CH2:54][CH:53]([C:56]2[C:64]3[C:59](=[CH:60][CH:61]=[C:62]([C:65]#[N:66])[CH:63]=3)[N:58](S(CC[Si](C)(C)C)(=O)=O)[CH:57]=2)[CH2:52][CH2:51]1)(=[O:49])=[O:48])=[O:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>Cl>[CH2:24]([O:31][NH:32][C:33]([C@H:35]1[CH2:40][N:39]([S:41]([N:44]([CH3:46])[CH3:45])(=[O:43])=[O:42])[CH2:38][CH2:37][N:36]1[S:47]([N:50]1[CH2:51][CH2:52][CH:53]([C:56]2[C:64]3[C:59](=[CH:60][CH:61]=[C:62]([C:65]#[N:66])[CH:63]=3)[NH:58][CH:57]=2)[CH2:54][CH2:55]1)(=[O:49])=[O:48])=[O:34])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 18727252HCID 18727252, compound

Product 1

HCID 18727253HCID 18727253, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tetrabutylammonium fluoride in tetrahydrofuran (1.54 ml, 1.54 mmol) was added to a solution of N-benzyloxy-1-{4-[5-cyano-1-(2-trimethylsilylethanesulfonyl)indole-3-yl]piperidine-1-sulfonyl}-4-(N,N-dimethylaminosulfonyl)piperazine-2-(R)-carboxamide (0.49 g, 0.62 mmol) and the reaction was placed in a 55° C. oil bath for 30 min. The reaction was diluted with 1 M HCl and concentrated in vacuo. The residue was extracted with ethyl acetate and the organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to give N-benzyloxy-1-[4-(5-cyanoindol-3-yl)piperidine-1-sulfonyl]-4-(N,N-dimethylamino-sulfonyl)piperazine-2-(R)-carboxamide (99%) as a tan solid. This material was converted to N-hydroxy-1-[4-(5-cyanoindol-3-yl)piperidine-1-sulfonyl]-4-(N,N-dimethylamino-sulfonyl)piperazine-2-(R)-carboxamide by following Example 16, Step 5.

Workup

  1. customwas placed in a 55° C.
  2. customfor 30 min
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3873310b6bd547b5b7079d9ce05f0646
Source dataset
uspto-grants-2000_11
Patent number
US06143744

Reaction notes

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