Methyl iodide → HCID 21098156, compound

HRID 1351387Notes

Reaction equation

HRID 1351387 reaction equation
[Li+].C[CH:3]([N-:5]C(C)C)C.CCCCCCC.C1COCC1.[CH2:21]([O:28][C:29]([N:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH:32]1[C:44](O)=O)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CI>C1COCC1>[C:3]([C:32]1([CH3:44])[CH2:33][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:41])[CH3:42])=[O:38])[CH2:35][CH2:36][N:31]1[C:29]([O:28][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:30])#[N:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 2756777N-4-Boc-N-1-Cbz-2-piperazine carboxylic acidHCID 21263495Tetrahydrofuran heptane

Product 1

HCID 21098156HCID 21098156, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-75 °C

Procedure

To a cooled (−75° C.) solution of LDA 2M in heptane/THF (1.5 eq) in THF, a solution of 1-[(benzyloxy)carbonyl]-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (Bigge et al, Tetrahedron Lett. 1989, 30: 5193) in THF was added dropwise at −75° C. After being stirred for 1 hour at −75° C., MeI (1.5 eq) was added. After 2 hours at −75°C. the reaction mixture was left warming to r.t., evaporated, diluted with AcOEt, washed with NaHCO3, water, brine and dried over Na2SO4. The crude was purified by flash chromatography on silica gel (petroleum ether/AcOEt, 85:15) to obtain the title compound.

Workup

  1. waitAfter 2 hours at −75°C. the reaction mixture was left
  2. temperaturewarming to r.t.
  3. customevaporated
  4. additiondiluted with AcOEt
  5. washwashed with NaHCO3, water, brine
  6. dry with materialdried over Na2SO4
  7. customThe crude was purified by flash chromatography on silica gel (petroleum ether/AcOEt, 85:15)

Sources & evidence

ORD record
ord-cefbaa6ee4814d488400cea7ea966136
Source dataset
uspto-grants-2007_05
Patent number
US07217713B2

Reaction notes

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