Acetonitrile → HCID 131731289, compound

HRID 1625648Notes

Reaction equation

HRID 1625648 reaction equation
[C:1]([Si:18](C)([CH3:25])[O:19][N-:20][C:21]([CH3:24])([CH3:23])[CH3:22])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[NH:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([OH:31])=[O:30].C(#N)C.N1CCCCC1.C(Cl)Cl>CO>[C:21]([N-:20][O:19][SiH:18]([CH3:25])[CH3:1])([CH3:24])([CH3:23])[CH3:22].[NH:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([OH:31])=[O:30]

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 6344DichloromethaneHCID 8082PiperidineHCID 131731291HCID 131731291, compound2×

Product 1

HCID 131731289HCID 131731289, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the thus-obtained Fmoc-t-butyl-dimethyl siloxy amide-L-proline (Compound 18) (1.18 g, 2.5 mmol), anhydrous acetonitrile (5 ml) and piperidine (2.4 ml) were added, and this was stirred for 1 hour at room temperature. After the completion of the reaction, acetonitrile (50 ml) was added to the mixture, and insoluble matters were removed by filtration. The solvent in the filtrate obtained was removed by evaporation under reduced pressure. The residual substance obtained was applied to silica gel column chromatography (the eluent: CH2Cl2:CH3OH=9:1). Thus, Compound 19 in the form of colorless syrup was obtained (0.61 g, yield: 90%). The result of NMR analysis with respect to this compound is shown below.

Workup

  1. additionwas added to the mixture, and insoluble matters
  2. customwere removed by filtration
  3. customThe solvent in the filtrate obtained
  4. customwas removed by evaporation under reduced pressure
  5. customThe residual substance obtained

Sources & evidence

ORD record
ord-bdd891628549425a8129d54e2a5f2c2e
Source dataset
uspto-grants-2014_07
Patent number
US08785121B2

Reaction notes

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