Tetrabutylammonium Fluoride → HCID 86578338, compound

HRID 629722Notes

Reaction equation

HRID 629722 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][C@H:31]1[O:36][CH2:35][C@@H:34]([CH2:37][N:38]2[CH:42]=[C:41]([Si](C)(C)C)[N:40]=[N:39]2)[NH:33][CH2:32]1)=[O:21])[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][C@H:31]1[O:36][CH2:35][C@@H:34]([CH2:37][N:38]2[CH:42]=[CH:41][N:40]=[N:39]2)[NH:33][CH2:32]1)=[O:21])[CH:7]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86578337HCID 86578337, compound

Product 1

HCID 86578338HCID 86578338, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Nα-(methoxycarbonyl)-β-phenyl-N-(2-{2-[(2R,5R)-5-{[4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl]methyl}morpholin-2-yl]ethyl}phenyl)-L-phenylalaninamide (1 eq.) in tetrahydrofuran (0.03M) was added TBAF (2.7 eq.). The reaction mixture was then heated to 50° C. for 16 hrs. The reaction mixture was quenched with aqueous saturated sodium bicarbonate. The aqueous layer was extracted with CH2Cl2 and the combined organic layers were dried over Na2SO4, filtered and concentrated. The evaporation residue was purified by automated silica gel flash chromatography system eluted with a gradient 0% to 30% of MeOH/EtOAc.

Workup

  1. customThe reaction mixture was quenched with aqueous saturated sodium bicarbonate
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe evaporation residue was purified by automated silica gel flash chromatography system
  7. washeluted with a gradient 0% to 30% of MeOH/EtOAc

Sources & evidence

ORD record
ord-6b92c3d1e2ae49fab973a5ed8926ea81
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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