2-Methylpentane → tert-butyl N-[3-(4-methoxyphenyl)propyl]-N-[(Z)-N-[(2-methylpropan-2-yl)oxycarbonyl]-C-pyrazol-1-ylcarbonimidoyl]carbamate

HRID 1183040Notes

Reaction equation

HRID 1183040 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30]O)=[CH:24][CH:23]=1.[C:32]([NH:39][C:40]([N:49]1[CH:53]=[CH:52][CH:51]=[N:50]1)=[N:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.CCCC(C)C>C(Cl)Cl>[C:45]([O:44][C:42](=[O:43])[N:41](/[C:40](=[N:39]/[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])/[N:49]1[CH:53]=[CH:52][CH:51]=[N:50]1)[CH2:30][CH2:29][CH2:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:27][CH:26]=1)([CH3:48])([CH3:47])[CH3:46]

Participants

7

Reactant 5

HCID 78922-MethylpentaneHCID 11776TriphenylphosphineHCID 794063-(4-Methoxyphenyl)-1-propanolHCID 97268Di-tert-butyl azodicarboxylateHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine

Product 1

HCID 87204231tert-butyl N-[3-(4-methoxyphenyl)propyl]-N-[(Z)-N-[(2-methylpropan-2-yl)oxycarbonyl]-C-pyrazol-1-ylcarbonimidoyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

PS-Triphenylphosphine (6.40 g, 12.03 mmol) is added to a solution of 3-(4-methoxyphenyl)-1-propanol (1.00 g, 6.02 mmol) in DCM (300 mL), followed by N,N′-di-Boc-1H-pyrazole-1-carboxamidine (1.87 g, 6.02 mmol). The reaction mixture is cooled to 4° C., and di-tert-butyl azodicarboxylate (1.39 g, 6.02 mmol) is added portionwise. The reaction is stirred for 5 minutes at 4° C., and then allowed to warm to RT. The resulting yellow suspension is stirred at RT overnight. The reaction is filtered to remove the PS-triphenylphosphine, which is rinsed with MeOH (20 mL). The combined filtrates are concentrated in vacuo to afford a colourless oil. iso-Hexane (50 mL) is added, and a fine cream solid precipitates out of solution, which is removed by filtration. The filtrate is concentrated in vacuo, and the resulting white solid is washed with iso-hexane (50 mL). The iso-hexane is concentrated in vacuo, and the resulting pale yellow oil is purified by chromatography (SiO2, EtOAc in iso-hexane, 0%-25%) to afford the title compound crude as a colourless oil. The oil is used in further reactions with no further purification. [M+H]+ 459.

Workup

  1. temperatureto warm to RT
  2. stirringThe resulting yellow suspension is stirred at RT overnight
  3. filtrationThe reaction is filtered
  4. customto remove the PS-triphenylphosphine, which
  5. washis rinsed with MeOH (20 mL)
  6. concentrationThe combined filtrates are concentrated in vacuo
  7. customto afford a colourless oil
  8. customa fine cream solid precipitates out of solution, which
  9. customis removed by filtration
  10. concentrationThe filtrate is concentrated in vacuo
  11. washthe resulting white solid is washed with iso-hexane (50 mL)
  12. concentrationThe iso-hexane is concentrated in vacuo
  13. customthe resulting pale yellow oil is purified by chromatography (SiO2, EtOAc in iso-hexane, 0%-25%)

Sources & evidence

ORD record
ord-62309cb441194932855ae184da0acf4d
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

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