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

HRID 1744140Notes

Reaction equation

HRID 1744140 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]([CH3:35])=[N:22][O:23][C:24]=3[NH:25][C@H:26]([C:31]([O:33]C)=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[C:21]([CH3:35])=[N:22][O:23][C:24]=3[NH:25][C@H:26]([C:31]([OH:33])=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69153222methyl N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucinate

Product 1

HCID 69152769N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucinate (450 mg, 0.926 mmol) in MeOH (15 mL) was added an aqueous solution of LiOH (2.0 M, 2.3 mL, 4.6 mmol) and the reaction mixture was stirred overnight. The reaction was acidified (pH=4–5) with aqueous 10% HCl, the product extracted with EtOAc (3×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (AcOH(EtOAc/Hex, 1/29/70) to afford N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucine.

Workup

  1. extractionthe product extracted with EtOAc (3×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (AcOH(EtOAc/Hex, 1/29/70)

Sources & evidence

ORD record
ord-0dece672c7e54352b2b941fef0a0ee01
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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