Acetonitrile → HCID 131731289, compound

HRID 1499388Notes

Reaction equation

HRID 1499388 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-7fd7c9ef0be847a09c1bf84c93c9dcd4
Source dataset
uspto-grants-2015_12
Patent number
US09200278B2

Reaction notes

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