Triethylamine → HCID 57425835, compound

HRID 1641498Notes

Reaction equation

HRID 1641498 reaction equation
C([NH:8][CH:9]1[CH2:12][CH:11]([CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]1[F:22])C1C=CC=CC=1.CCN(CC)CC.[N+](C1C=CC([N:39]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:40](=[O:42])[O-])=CC=1)([O-])=O>C(Cl)Cl>[CH2:43]([NH:39][C:40]([NH:8][CH:9]1[CH2:12][CH:11]([CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]1[F:22])=[O:42])[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53443327HCID 53443327, compoundHCID 57425834HCID 57425834, compound

Product 1

HCID 57425835HCID 57425835, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 25 mL flask with benzyl-(3-benzyloxymethyl-2-fluoro-cyclobutyl)-amine (25.8 mg, 0.12 mmol) inside, dry CH2Cl2 2 mL was added under argon at room temperature to give a colorless solution, followed by the addition of Et3N (0.02 mL, 0.14 mmol). After stirring for 5 min, 4-nitrophenyl-N-benzylcarbamate (32.1 mg, 0.12 mmol) was added to give a yellow solution. This was left stirring at room temperature for 10 hr and the reaction was quenched by adding 10 mL CH2Cl2. The organic phase was washed with 1 M NaOH 10 mL, H2O 10 mL and brine 10 mL and was dried over MgSO4. Solvent evaporation gave the crude product 42 mg that is pure enough and crystallization gave the pure product 38 mg (90%) as a white solid.

Workup

  1. customto give a colorless solution
  2. customto give a yellow solution
  3. waitThis was left
  4. stirringstirring at room temperature for 10 hr
  5. customthe reaction was quenched
  6. additionby adding 10 mL CH2Cl2
  7. washThe organic phase was washed with 1 M NaOH 10 mL, H2O 10 mL and brine 10 mL
  8. dry with materialwas dried over MgSO4
  9. customSolvent evaporation
  10. customgave the crude product 42 mg that
  11. customcrystallization

Sources & evidence

ORD record
ord-e271f44261c54fdcb876ab51fc4ceb3d
Source dataset
uspto-grants-2012_02
Patent number
US08114994B2

Reaction notes

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