Dichloromethane → HCID 58202514, compound

HRID 1045090Notes

Reaction equation

HRID 1045090 reaction equation
[C:1]1(=N)[C:13]2[C:5]([C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:4][CH:3]=[CH:2]1.Cl.[C:16]([O:20][C:21](=[O:24])[CH2:22][NH2:23])([CH3:19])([CH3:18])[CH3:17].C(Cl)Cl>C(OCC)C.CCCCCC>[C:16]([O:20][C:21](=[O:24])[CH2:22][N:23]=[C:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 86652224HCID 86652224, compound

Product 1

HCID 58202514HCID 58202514, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

The fluorenone imine (1.52 g, 8.48 mmol) and the glycine tert-butylester hydrochloride (1.42 g, 8.48 mmol) were stirred in the methylene chloride for five hours at room temperature. The reaction solution was filtered with celite, and the solvent was removed by the distillation under reduced pressure. The obtained residual was allowed to dissolve in the diethyl ether. And, it was filtered with the celite. The obtained ether solution was cleaned with water and a saturated sodium chloride aqueous solution. And, it was dried over sodium sulfate. After the filtering and the concentration under reduced pressure were conducted, the obtained crude product was refined with the diethyl ether/hexane (recrystallization). And, (Fluoren-9-ylideneamino)-acetic acid tert-butyl ester (1.18 g, 66%) was obtained.

Workup

  1. filtrationThe reaction solution was filtered with celite
  2. customthe solvent was removed by the distillation under reduced pressure
  3. dissolutionto dissolve in the diethyl ether
  4. filtrationAnd, it was filtered with the celite
  5. dry with materialAnd, it was dried over sodium sulfate
  6. concentrationAfter the filtering and the concentration under reduced pressure
  7. customthe obtained crude product

Sources & evidence

ORD record
ord-fa2ccbbdd5b149b48d56264b02bd7e57
Source dataset
uspto-grants-2013_10
Patent number
US08563765B2

Reaction notes

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