Tetrabutylammonium Fluoride → HCID 90370238, compound

HRID 2176001Notes

Reaction equation

HRID 2176001 reaction equation
[Si]([O:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([CH:57]=[CH:58][CH:59]=1)[C:24]([NH:26][C:27]1[S:28][C:29]2[CH2:56][CH2:55][CH2:54][CH2:53][C:30]=2[C:31]=1[C:32]([NH:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][C:43]2[CH:52]=[CH:51][C:46]([C:47]([O:49][CH3:50])=[O:48])=[CH:45][CH:44]=2)=[CH:37][CH:36]=1)=[O:33])=[O:25])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([CH:57]=[CH:58][CH:59]=1)[C:24]([NH:26][C:27]1[S:28][C:29]2[CH2:56][CH2:55][CH2:54][CH2:53][C:30]=2[C:31]=1[C:32]([NH:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][C:43]2[CH:44]=[CH:45][C:46]([C:47]([O:49][CH3:50])=[O:48])=[CH:51][CH:52]=2)=[CH:37][CH:36]=1)=[O:33])=[O:25]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90370352HCID 90370352, compound

Product 1

HCID 90370238HCID 90370238, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 830 mg of methyl 4-[2-(4-{[(2-{[3-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate and 10 mL of THF was added 1.5 mL of tetrabutylammonium fluoride (TBAF) (1.0 M THF solution) under ice cooling, followed by stirring for 4 hours at room temperature and then overnight at 50° C. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (10% methanol/chloroform), thereby obtaining 540 mg of methyl 4-[2-(4-{[(2-{[3-(2-hydroxyethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate.

Workup

  1. customovernight
  2. customat 50° C
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (10% methanol/chloroform)

Sources & evidence

ORD record
ord-8d1c10065b5743e796208248efe63470
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

Loading…