Water → HCID 68196374, compound

HRID 1626809Notes

Reaction equation

HRID 1626809 reaction equation
[CH2:1]([O:3][C:4](=[O:55])[CH2:5][NH:6][C:7]([C:9]1[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:13]([CH3:23])[N:12]=[C:11]([CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][C:34]([CH2:37][C:38]4[CH:39]=[N:40][C:41]([O:44][CH2:45][CH2:46][O:47][Si](C(C)(C)C)(C)C)=[CH:42][CH:43]=4)=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[N:10]=1)=[O:8])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:55])[CH2:5][NH:6][C:7]([C:9]1[C:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:13]([CH3:23])[N:12]=[C:11]([CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:32]=[CH:33][C:34]([CH2:37][C:38]4[CH:39]=[N:40][C:41]([O:44][CH2:45][CH2:46][OH:47])=[CH:42][CH:43]=4)=[CH:35][CH:36]=3)[CH2:27][CH2:26]2)[N:10]=1)=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 68196373HCID 68196373, compound

Product 1

HCID 68196374HCID 68196374, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A crude product of ethyl({[5-(benzyloxy)-2-{[1-(4-{[6-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)pyridin-3-yl]methyl}phenyl)piperidin-4-yl]methyl}-6-methylpyrimidin-4-yl]carbonyl}amino)acetate was dissolved in tetrahydrofuran (20 mL), and a solution of tetrabutylammonium fluoride in tetrahydrofuran (1.0 M, 1.4 mL, 4.8 mmol) was added at 0° C., followed by stirring at the same temperature for 1 hour. Water was added to the reaction solution, followed by extraction with ethyl acetate, and subsequently the organic layer was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.50 (ethyl acetate) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.31 g, 0.47 mmol) as a yellow oil (yield 66%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. concentrationsubsequently the organic layer was concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  4. concentrationa fraction corresponding to the Rf value=0.50 (ethyl acetate) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e7e020e99c1241f0a62f7dbc4907257a
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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