Ethanol → HCID 67048530, compound

HRID 551210Notes

Reaction equation

HRID 551210 reaction equation
[CH:1]1([NH2+]C2CCCCC2)CCCC[CH2:2]1.[CH2:14]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][CH2:30][C:31]#[N:32])[C:26]([O-:28])=[O:27])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C(O)C>C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:14]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][CH2:30][C:31]#[N:32])[C:26]([O:28][CH2:1][CH3:2])=[O:27])=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66731963HCID 66731963, compound

Product 1

HCID 67048530HCID 67048530, compound

Reagents, catalysts & solvents 1

HCID 311Citric AcidSolvent

Procedure

5.00 g (11.3 mmol) dicyclohexylammonium-(2S)-2-(benzyloxycarbonyl-amino)-4-cyano-butanoate are stirred into in 100 ml of 5% citric acid solution and then extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and the solvent is distilled off i. vac. The residue is dissolved in 70 ml THF, 4.35 g (13.5 mmol) TBTU and 6.35 ml (33.8 mmol) DIPEA are added and the mixture is stirred for 10 minutes at ambient temperature. Then 50 ml of ethanol are added and the mixture is refluxed for 16 hours. Then the reaction mixture is evaporated down i. vac., taken up in ethyl acetate, washed with semisaturated sodium hydrogen carbonate solution and water, dried over sodium sulphate and evaporated down i. vac.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. distillationthe solvent is distilled off i
  4. dissolutionThe residue is dissolved in 70 ml THF
  5. temperaturethe mixture is refluxed for 16 hours
  6. customThen the reaction mixture is evaporated down i
  7. washwashed with semisaturated sodium hydrogen carbonate solution and water
  8. dry with materialdried over sodium sulphate
  9. customevaporated down i

Sources & evidence

ORD record
ord-f7ed3619ce4042c5bd93bef33ddc082e
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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