Monobasic potassium phosphate → methyl N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucinate

HRID 1744125Notes

Reaction equation

HRID 1744125 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:21]([N:25](C(OCC(Cl)(Cl)Cl)=O)[C@H:26]([C:31]([O:33][CH3:34])=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])=[N:22][O:23][N:24]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].OP([O-])(O)=O.[K+]>C1COCC1.[Zn]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[C:21]([NH:25][C@H:26]([C:31]([O:33][CH3:34])=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])=[N:22][O:23][N:24]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 516951Monobasic potassium phosphate2×HCID 69152043methyl N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate

Product 1

HCID 69151159methyl N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucinate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To methyl N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate (605 mg, 0.932 mmol) in THF (20 mL) was added activated zinc powder (610 mg, 9.32 mmol) and an aqueous solution of KH2PO4 (1.0 M, 1.8 mL, 1.8 mmol) dropwise. After 15 min an additional aliquot of aqueous KH2PO4 solution was added (1.0 M, 1.8 mL, 1.8 mmol) and the reaction mixture was stirred for 4 hours. The zinc powder was filtered off, rinsed with Et2O and water and the product extracted with ether (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (EtOAc/Hex, 25/5) to afford methyl N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucinate.

Workup

  1. filtrationThe zinc powder was filtered off
  2. washrinsed with Et2O and water
  3. extractionthe product extracted with ether (2×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography over silica gel (EtOAc/Hex, 25/5)

Sources & evidence

ORD record
ord-9708e89992a046459bba3c9c4d3b6f8e
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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