Triethylamine → HCID 57656764, compound

HRID 603196Notes

Reaction equation

HRID 603196 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[C@@H:6]([C:17]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:18])[CH2:5]1)([CH3:3])[CH3:2].[CH2:25]([O:32][C:33]1[CH:34]=[C:35]([NH:39][C:40](=O)[O:41]C2C=CC=CC=2)[CH:36]=[CH:37][CH:38]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C1COCC1>[CH2:25]([O:32][C:33]1[CH:34]=[C:35]([NH:39][C:40]([N:22]2[CH2:21][CH2:20][N:19]([C:17]([C@H:6]3[CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8][NH:7]3)=[O:18])[CH2:24][CH2:23]2)=[O:41])[CH:36]=[CH:37][CH:38]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57656651HCID 57656651, compoundHCID 57656692HCID 57656692, compound

Product 1

HCID 57656764HCID 57656764, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of tert-butyl (2R)-4-isopropyl-2-(piperazin-1-ylcarbonyl)piperazine-1-carboxylate (0.2 g, 0.59 mmol) and phenyl [3-(benzyloxy)phenyl]carbamate (0.189 g, 0.59 mmol) in THF (5 μL) was added triethylamine (91 uL, 0.65 mmol) and the reaction heated to 60° C. for 6 hours. The solvents were then removed in vacuo and the residue dissolved in DCM (3 ml), added TFA (3 ml) and stirred at room temperature for a further 90 mins. The reaction mixture was then concentrated under reduced pressure, residue partitioned between DCM/1M NaOH, extracted twice, combined organics passed through phase separating cartridge and evaporated to dryness to give a yellow gum. This was then purified by silica gel chromatography (Isco Companion™; 12 g column; 10% methanolic ammonia/DCM)

Workup

  1. customThe solvents were then removed in vacuo
  2. dissolutionthe residue dissolved in DCM (3 ml)
  3. additionadded TFA (3 ml)
  4. concentrationThe reaction mixture was then concentrated under reduced pressure, residue
  5. custompartitioned between DCM/1M NaOH
  6. extractionextracted twice
  7. customseparating cartridge
  8. customevaporated to dryness
  9. customto give a yellow gum
  10. customThis was then purified by silica gel chromatography (Isco Companion™; 12 g column; 10% methanolic ammonia/DCM)

Sources & evidence

ORD record
ord-ebf9bf1594c14066bd77ccf5d1199458
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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