Tert-Butylamine → 1-(benzyloxycarbonyl)-4-(tert.butoxycarbonyl)-N-tert.butyl-2-piperazinecarboxamide

HRID 54098Notes

Reaction equation

HRID 54098 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[C:24](O)=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCOCC1)C.ClC(OCC(C)C)=O.[C:43]([NH2:47])([CH3:46])([CH3:45])[CH3:44]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:13][CH:12]1[C:24]([NH:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:25])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 2756777N-4-Boc-N-1-Cbz-2-piperazine carboxylic acid

Product 1

HCID 190319381-(benzyloxycarbonyl)-4-(tert.butoxycarbonyl)-N-tert.butyl-2-piperazinecarboxamideYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

0.285 g of 1-(benzyloxycarbonyl)-4-(tert.butoxycarbonyl)-2-piperazinecarboxylic acid was dissolved in 10 ml of dry tetrahydrofuran and cooled to -15° C. while stirring. There was then added 0.09 g of N-ethylmorpholine followed immediately by 0.107 g of isobutyl chloroformate. The mixture was stirred for 5 minutes and then 0.2 g of tert.butylamine was added dropwise. Stirring was continued overnight, during which time the mixture was allowed to reach room temperature. The solvent was removed by evaporation and there was obtained a buff coloured oil which was partitioned between ethyl acetate and water. The organic phase was washed in sequence with 10% citric acid solution, sodium bicarbonate solution and saturated sodium chloride solution and dried over anhydrous sodium sulphate. The solvent was removed by evaporation to give 0.185 g of 1-(benzyloxycarbonyl)-4-(tert.butoxycarbonyl)-N-tert.butyl-2-piperazinecarboxamide as a light brown oil; MS: m/e 420 [M+H]+.

Workup

  1. stirringThe mixture was stirred for 5 minutes
  2. stirringStirring
  3. customto reach room temperature
  4. customThe solvent was removed by evaporation
  5. customthere was obtained a buff coloured oil which
  6. customwas partitioned between ethyl acetate and water
  7. washThe organic phase was washed in sequence with 10% citric acid solution, sodium bicarbonate solution and saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulphate
  9. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-0b8f546ead9145cebe2b5b61c4cbb5ae
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

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