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Phenylacetic Acid → Tert-butyl (3s)-3-methyl-4-(phenylacetyl)piperazine-1-carboxylate

HRID 38269
Notes
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Reaction equation

HRID 38269 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[C:15]1([CH2:21][C:22](O)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH3:1][C@@H:2]1[N:7]([C:22](=[O:23])[CH2:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 999Phenylacetic AcidHCID 81531DiisopropylethylamineHCID 7023035(S)-1-Boc-3-methylpiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67131985Tert-butyl (3s)-3-methyl-4-(phenylacetyl)piperazine-1-carboxylate
Yield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methyl-(3S)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (250 mg), benzeneacetic acid (210 mg) and Hunigs base (450 □l) were dissolved in DMF (10 ml) and HATU (720 mg) added portionwise over 2 min. The reaction mixture was stirred for 3 h, diluted with EtOAc, washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica with 25% EtOAc/isohexane as eluent to give the sub-title compound (330 mg)

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica with 25% EtOAc/isohexane as eluent

Sources & evidence

ORD record
ord-1732818959bb4e6aa79ac33906d948fb
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524715B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes