HCID 86748357, compound → HCID 18925459, compound

HRID 1289102Notes

Reaction equation

HRID 1289102 reaction equation
[C:1]([C:4]1[CH:34]=[CH:33][C:7]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([O:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])[CH2:20][CH2:19]2)=[O:17])=[O:9])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2]>ClCCl.FC(F)(F)C(O)=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([O:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:20][CH2:19]2)=[O:17])=[O:9])=[CH:33][CH:34]=1)(=[NH:2])[NH2:3]

Participants

4

Reactant 1

HCID 86748357HCID 86748357, compound

Product 1

HCID 18925459HCID 18925459, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 700 mg of t-butyl [[1-[[1-(p-amidinobenzoyl)-2-piperidinyl]carbonyl]-4-piperidinyl]oxy]acetate in 20 ml of dichloromethane and 20 ml of trifluoroacetic acid is stirred at room temperature for 3 hours and evaporated. The residue is dissolved in ethanol and treated with ether. Suction filtration and drying of the precipitate and chromatography on silica gel (RP-18, water/THF 9:1) gives 111 mg of [[1-[[1-(p-amidino-benzoyl)-2-piperidinyl]carbonyl]-4-piperidinyl]oxyacetic acid. M.p. 233°-234° C.

Workup

  1. customevaporated
  2. dissolutionThe residue is dissolved in ethanol
  3. additiontreated with ether
  4. filtrationSuction filtration
  5. customdrying of the precipitate and chromatography on silica gel (RP-18, water/THF 9:1)

Sources & evidence

ORD record
ord-27fc52ab7e9f44f98446b0c9aeaf1ec9
Source dataset
uspto-grants-1998_05
Patent number
US05747522

Reaction notes

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