Tetrabutylammonium Fluoride → HCID 69061845, compound

HRID 7323Notes

Reaction equation

HRID 7323 reaction equation
[Si]([O:18][C:19]1[CH:20]=[C:21](/[CH:26]=[CH:27]/[S:28]([NH:31][C@H:32]2[CH2:36][CH2:35][N:34]([C@@H:37]([CH3:46])[C:38]([N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)=[O:39])[C:33]2=[O:47])(=[O:30])=[O:29])[CH:22]=[CH:23][C:24]=1[Cl:25])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:25][C:24]1[CH:23]=[CH:22][C:21](/[CH:26]=[CH:27]/[S:28]([NH:31][C@H:32]2[CH2:36][CH2:35][N:34]([C@@H:37]([CH3:46])[C:38]([N:40]3[CH2:41][CH2:42][O:43][CH2:44][CH2:45]3)=[O:39])[C:33]2=[O:47])(=[O:30])=[O:29])=[CH:20][C:19]=1[OH:18]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69057675(E)-2-(3-{[tert-butyl(diphenyl)silyl]oxy}-4-chlorophenyl)-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}ethenesulfonamide

Product 1

HCID 69061845HCID 69061845, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-2-(3-{[tert-butyl(diphenyl)silyl]oxy}-4-chlorophenyl)-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}ethenesulfonamide (0.0078 g) in THF (0.3 ml) at −78° C. under nitrogen, tetra n-butylammonium fluoride (1M in THF, 0.014 ml) was added. The mixture was allowed to warm to room tempertaure over 3 days and then concentrated under reduced pressure. The residue was purified using mass directed preparative h.p.l.c. to give the title compound (0.0043 g) as a clear film.

Workup

  1. temperatureto warm to room tempertaure over 3 days
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified

Sources & evidence

ORD record
ord-bce6d1b0269345ada7d58941bda39329
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Reaction notes

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