Trifluoroacetic acid → HCID 19067141, compound

HRID 481773Notes

Reaction equation

HRID 481773 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]([CH3:17])[CH2:15][CH:14]([O:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH2:13][CH:12]1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH:16]([CH3:17])[CH2:15][CH:14]([O:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:13][CH:12]1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19067143HCID 19067143, compound

Product 1

HCID 19067141HCID 19067141, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.11 g of N-benzyloxycarbonyl-4-tert-butoxycarbonylmethyloxy-2,6-dimethylpiperidine was dissolved in 5 ml of methylene chloride, and 2 ml of trifluoroacetic acid was added. The solution was stirred overnight at room temperature, and the resulting solution was concentrated under reduced pressure. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography. From the fractions eluted with chloroform-methanol (9:1 v/v) was obtained 0.61 g of N-benzyloxycarbonyl-4-carboxymethyloxy-2,6-dimethylpiperidine, which was an oily product with no color (yield: 65%).

Workup

  1. concentrationthe resulting solution was concentrated under reduced pressure
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography
  4. washFrom the fractions eluted with chloroform-methanol (9:1 v/v)

Sources & evidence

ORD record
ord-d3466d0402c64911a564a5a53fd18566
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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