Tetrabutylammonium Fluoride → HCID 24884784, compound

HRID 901958Notes

Reaction equation

HRID 901958 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][NH:29][C:30]([CH:32]1[O:37][C:36]2[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=2[N:34]([C:42]([C:44]2[S:45][CH:46]=[C:47]([CH2:50][N:51]([S:53]([C:56]3[CH:61]=[CH:60][C:59]([Cl:62])=[CH:58][CH:57]=3)(=[O:55])=[O:54])[CH3:52])[C:48]=2[Cl:49])=[O:43])[CH2:33]1)=[O:31])(C(C)(C)C)(C)C>C1COCC1.C(OCC)(=O)C>[Cl:49][C:48]1[C:47]([CH2:50][N:51]([S:53]([C:56]2[CH:61]=[CH:60][C:59]([Cl:62])=[CH:58][CH:57]=2)(=[O:55])=[O:54])[CH3:52])=[CH:46][S:45][C:44]=1[C:42]([N:34]1[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[O:37][CH:32]([C:30]([NH:29][CH2:28][CH2:27][OH:26])=[O:31])[CH2:33]1)=[O:43]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69208383HCID 69208383, compound

Product 1

HCID 24884784HCID 24884784, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tetrabutylammonium fluoride in THF (1.0M, 1.0 ml, 11.0 mmol) was added to a solution of N-(2-tert-butyldimethylsilyloxyethyl)-4-(3-chloro-4-(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carbonyl)benzomorpholine-2-carboxamide (65 mg, 0.093 mmol) in THF (4.0 ml) and stirred for 1 h. The mixture was reduced, taken up in ethyl acetate, washed with 1N hydrochloric acid and brine, filtered and reduced. Chromatography (95% 60-80 petroleum ether/5% EtOAc) afforded 4-(3-chloro-4-(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carbonyl)-N-(2-hydroxyethyl)-benzomorpholine-2-carboxamide as a white solid (25 mg, 46%).

Workup

  1. washwashed with 1N hydrochloric acid and brine
  2. filtrationfiltered

Sources & evidence

ORD record
ord-b2eb307a63e343f391059bf7efd6f837
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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