L-Malic Acid → HCID 131722769, compound

HRID 1384877Notes

Reaction equation

HRID 1384877 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:50][N:51]2[CH:55]=[N:54][CH:53]=[N:52]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]([CH:40]([C:47]([OH:49])=[O:48])[CH2:41][NH:42][CH:43]([CH3:46])[CH2:44][CH3:45])[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.[OH:56][C@@H:57]([CH2:61][C:62]([OH:64])=[O:63])[C:58]([OH:60])=[O:59]>C(O)C>[OH:56][C@@H:57]([CH2:61][C:62]([OH:64])=[O:63])[C:58]([OH:60])=[O:59].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:50][N:51]2[CH:55]=[N:54][CH:53]=[N:52]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:29]=[CH:30][C:31]([N:34]5[C:38](=[O:39])[N:37]([CH:40]([C:47]([OH:49])=[O:48])[CH2:41][NH:42][CH:43]([CH3:46])[CH2:44][CH3:45])[N:36]=[CH:35]5)=[CH:32][CH:33]=4)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH2:11][O:10]1

Participants

4

Reactant 2

HCID 222656L-Malic AcidHCID 131722770HCID 131722770, compound

Product 1

HCID 131722769HCID 131722769, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[2S-[2α,4[(R*,R*)]]]-2-[4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-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 β-alanine (0.0028 mol) was dissolved in warm ethanol (25 ml). (−)-(S)-hydroxybutanedioic acid (0.0061 mol) was added and the mixture was parboiled until complete dissolution. The resulting clear solution was allowed to cool to room temperature and the solvent was evaporated. The residue was stirred in 2-propanone, filtered off, then dried, yielding 1.53 g (53%) [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 β-alanine (S)-hydroxybutanedioate(1:2) monohydrate (compound 12).

Workup

  1. dissolutionthe mixture was parboiled until complete dissolution
  2. customthe solvent was evaporated
  3. filtrationfiltered off
  4. customdried

Sources & evidence

ORD record
ord-16ea15d8432646efa42c4be806df6d2b
Source dataset
uspto-grants-2001_07
Patent number
US06262052B1

Reaction notes

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