Maleic Acid → 2-[4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]-phenyl]-1-piperazinyl]-phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]-1-methylpropyl L-phenylalanine (Z)-2-butenedioate

HRID 48480Notes

Reaction equation

HRID 48480 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:56][N:57]2[CH:61]=[N:60][CH:59]=[N:58]2)[O:13][CH:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([N:34]5[C:38](=[O:39])[N:37]([C:40]6[CH:55]=[CH:54][CH:53]=[CH:52][C:41]=6[CH2:42][C@@H:43]([C:49]([OH:51])=[O:50])[NH:44][CH:45]([CH3:48])[CH2:46][CH3:47])[N:36]=[CH:35]5)=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH2:11][O:10]1.[C:62]([OH:69])(=[O:68])/[CH:63]=[CH:64]\[C:65]([OH:67])=[O:66]>CC(=O)C>[C:62]([OH:69])(=[O:68])/[CH:63]=[CH:64]\[C:65]([OH:67])=[O:66].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:56][N:57]2[CH:61]=[N:60][CH:59]=[N:58]2)[O:13][CH:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([N:34]5[C:38](=[O:39])[N:37]([C:40]6[CH:55]=[CH:54][CH:53]=[CH:52][C:41]=6[CH2:42][C@@H:43]([C:49]([OH:51])=[O:50])[NH:44][CH:45]([CH3:48])[CH2:46][CH3:47])[N:36]=[CH:35]5)=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH2:11][O:10]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 698850272-[4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]-phenyl]-1-piperazinyl]-phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]-1-methylpropyl L-phenylalanine

Product 1

HCID 865839502-[4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]-phenyl]-1-piperazinyl]-phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]-1-methylpropyl L-phenylalanine (Z)-2-butenedioate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Compound 23 (0.00359 mol) was dissolved in 2-propanone (25 ml). A solution of (Z)-2-butenedioic acid (0.00359 mol) in 2-propanone (5 ml) was added. The mixture was stirred for 16 hours. The precipitate was filtered off, washed with 2-propanone (2.5 ml), and dried, yielding 3.12 g [2S-[2α,4α[(R*,R*)]]]-2-[4-[4-[4-[4[[-2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]-phenyl]-1-piperazinyl]-phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]-1-methylpropyl L-phenylalanine (Z)-2-butenedioate (1:1) (compound 25).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with 2-propanone (2.5 ml)
  3. customdried

Sources & evidence

ORD record
ord-b5af2f7551594da48377c07807c40d17
Source dataset
uspto-grants-2004_03
Patent number
US06703506B2

Reaction notes

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