HCID 69100654, compound → HCID 69100742, compound

HRID 394011Notes

Reaction equation

HRID 394011 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][C@H:18]1[CH2:23][CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]1)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.FC(F)(F)C(O)=O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][C@H:18]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69100654HCID 69100654, compound

Product 1

HCID 69100742HCID 69100742, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 1.84 g of 3-(benzyloxycarbonyl)amino-N-({(3R)-1-(tert-butoxycarbonyl)-3-piperidyl}methyl)propanamide in 2 ml of chloroform, 2 ml of trifluoroacetic acid was added at room temperature, followed by an hour's stirring at the same temperature. The reaction liquid was distilled off under reduced pressure, and the residue was rendered basic with, 4N aqueous sodium hydroxide solution. Extracting the product with chloroform, the product was dried over anhydrous sodium sulfate. Upon distilling the solvent off under reduced pressure, 1.26 g of the title compound was obtained.

Workup

  1. waitfollowed by an hour
  2. customThe reaction liquid
  3. distillationwas distilled off under reduced pressure
  4. extractionExtracting the product with chloroform
  5. dry with materialthe product was dried over anhydrous sodium sulfate
  6. distillationUpon distilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-4e0364a866e3457c9728ed460013eb6c
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

Loading…