N-(tert-butoxycarbonyl)glycine → {2-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethyl}-carbamic Acid tert-butyl Ester

HRID 11685Notes

Reaction equation

HRID 11685 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[F:25][C:26]1[CH:40]=[CH:39][C:29]([CH2:30][N:31]2[CH2:36][C@H:35]([CH3:37])[NH:34][CH2:33][C@H:32]2[CH3:38])=[CH:28][CH:27]=1>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]([N:34]1[CH2:33][C@H:32]([CH3:38])[N:31]([CH2:30][C:29]2[CH:39]=[CH:40][C:26]([F:25])=[CH:27][CH:28]=2)[CH2:36][C@H:35]1[CH3:37])=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23405839(2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine

Product 1

HCID 69655545{2-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethyl}-carbamic Acid tert-butyl EsterYield 94.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butoxycarbonylamino-acetic acid (0.71 g, 4.05 mmol) in dichloromethane (40 mL) was added 4-dimethylaminopyridine (0.74 g, 6.07 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.16 g, 6.07 mmol) and 1-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazine (0.90 g, 4.05 mmol). The reaction was stirred overnight at ambient temperature. The reaction was diluted with dichloromethane and washed with brine. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (1.45 g).

Workup

  1. washwashed with brine
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7f1d605a00c407485160438a0416ec8
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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