tert-Butyl piperazine-1-carboxylate → HCID 67774159, compound

HRID 1963081Notes

Reaction equation

HRID 1963081 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:13]([C:31](O)=[O:32])=[C:14]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=3[CH3:30])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=[CH:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[CH2:11]([O:10][C:8]([C:7]1[CH:6]=[N:5][N:4]2[C:13]([C:31]([N:44]3[CH2:43][CH2:42][N:41]([C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])[CH2:46][CH2:45]3)=[O:32])=[C:14]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=3[CH3:30])[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:3]2[C:2]=1[Cl:1])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67774375HCID 67774375, compound

Product 1

HCID 67774159HCID 67774159, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of step 8 (2.335 g, 5.00 mmol), 1-tert-butoxycarbonyl-piperazine (1.024 g, 5.50 mmol), EDIA (2.18 ml, 12.50 mmol) and TBTU (1.766 g, 5.50 mmol) in 50 ml of anhydrous DCM were stirred at room temperature for 1 h. The solution was then washed with 0.5 N hydrochloric acid (75 ml) and the aqueous phase was extracted with DCM (25 ml). The combined organic phases were washed with a saturated solution of sodium hydrogencarbonate (50 ml) and brine (50 ml), dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 80:20, then 75:25) to give 3.01 g of the title compound as a yellow solid melting at 88-90° C.

Workup

  1. washThe solution was then washed with 0.5 N hydrochloric acid (75 ml)
  2. extractionthe aqueous phase was extracted with DCM (25 ml)
  3. washThe combined organic phases were washed with a saturated solution of sodium hydrogencarbonate (50 ml) and brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 80:20

Sources & evidence

ORD record
ord-e7a5ef9ba98b414184274bb5dbfe06ca
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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