Hydrochloric Acid → N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucine

HRID 1744126Notes

Reaction equation

HRID 1744126 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]([NH:25][C@H:26]([C:31]([O:33]C)=[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].[Li+].[OH-].Cl>CO.[Cl-].[Na+].O>[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]([OH:33])=[O:32])[CH2:27][CH:28]([CH3:29])[CH3:30])=[N:22][O:23][N:24]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 69151159methyl N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucinate

Product 1

HCID 69151656N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To methyl N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucinate (375 mg, 0.793 mmol) in MeOH (20 mL) was added an aqueous solution of LiOH (2.0 M, 2.0 mL, 4.0 mmol) and the reaction mixture was stirred for 2 hours. An additional aliquot of aqueous LiOH (2.0 M, 2.0 mL, 4.0 mmol) was added and the reaction mixture was stirred for 1 hour. The reaction was acidified (pH=4–5) with aqueous 10% HCl, brine was added and the product extracted with EtOAc (3×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (Hex/EtOAc/AcOH, 50/49/1) to afford N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucine.

Workup

  1. stirringthe reaction mixture was stirred for 1 hour
  2. additionwas added
  3. extractionthe product extracted with EtOAc (3×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography over silica gel (Hex/EtOAc/AcOH, 50/49/1)

Sources & evidence

ORD record
ord-56ce823766f047b180225e557a74db0f
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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