HCID 66920241, compound → HCID 66920030, compound

HRID 1908633Notes

Reaction equation

HRID 1908633 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([CH2:10][O:11][C:12]2[N:13]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:14]=[C:15]([C:17](=[O:47])[NH:18][C@H:19]([C:29]([N:31]3[CH2:36][CH2:35][N:34]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:38]=4)[CH2:33][CH2:32]3)=[O:30])[CH2:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])[CH:16]=2)=[CH:8][CH:9]=1)=[O:4]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([CH2:10][O:11][C:12]2[N:13]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:14]=[C:15]([C:17](=[O:47])[NH:18][C@H:19]([C:29]([N:31]3[CH2:32][CH2:33][N:34]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:44])[F:45])[CH:38]=4)[CH2:35][CH2:36]3)=[O:30])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:16]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 66920241HCID 66920241, compound

Product 1

HCID 66920030HCID 66920030, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The crude 5-(5-{(S)-3-tert-Butoxycarbonyl-1-[4-(3-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-propylcarbamoyl}-2-phenyl-2H-pyrazol-3-yloxymethyl)-furan-2-carboxylic acid methyl ester was dissolved in a mixture of 2 ml of DCM and 1 ml of TFA. After 2 h at RT all volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a white solid.

Workup

  1. customAfter 2 h at RT all volatiles were removed under reduced pressure
  2. customthe residue was purified by preparative HPLC (
  3. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
  4. additionThe fractions containing the product
  5. customwere evaporated
  6. customto yield a white solid

Sources & evidence

ORD record
ord-b3c13b510d174526b2f97a3f6a76847a
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

Loading…