1-Benzylpiperazine → 3-(beta-D-Galactopyranosyloxy)-5-isopropyl-4-{[4-(3-{1-[(piperazin-1-yl)carbonyl]-1-(methyl)-ethylcarbamoyl}propoxy)-2-methylphenyl]methyl}-1H-pyrazole

HRID 1442449Notes

Reaction equation

C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][C:41](=[O:49])[NH:42][C:43](C(O)=O)([CH3:45])[CH3:44])=[CH:33][C:32]=2[CH3:50])=[C:28]([CH:51]([CH3:53])[CH3:52])[NH:27][N:26]=1)(=O)C.C(O[C:62]([N:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1)=[O:63])C1C=CC=CC=1.C(N1CCNCC1)C1C=CC=CC=1>>[C@@H:6]1([O:24][C:25]2[C:29]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][C:41](=[O:49])[NH:42][C:43]([C:62]([N:64]4[CH2:65][CH2:66][NH:67][CH2:68][CH2:69]4)=[O:63])([CH3:44])[CH3:45])=[CH:33][C:32]=3[CH3:50])=[C:28]([CH:51]([CH3:53])[CH3:52])[NH:27][N:26]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

Reactant 3

HCID 759941-Benzylpiperazine

HCID 643495Benzyl piperazine-1-carboxylate

HCID 68538260HCID 68538260, compound

Product 1

HCID 117648123-(beta-D-Galactopyranosyloxy)-5-isopropyl-4-{[4-(3-{1-[(piperazin-1-yl)carbonyl]-1-(methyl)-ethylcarbamoyl}propoxy)-2-methylphenyl]methyl}-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Example 99 using 3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-[(4-{3-[1-carboxy-1-(methyl)-ethylcarbamoyl]propoxy}-2-methylphenyl)methyl]-5-isopropyl-1H-pyrazole and 1-(benzyloxycarbonyl)piperazine instead of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-[(4-{2-[1-carboxy-1-(methyl)ethylcarbamoyl]ethoxy}-2-methyl-phenyl)methyl]-5-isopropyl-1H-pyrazole and 1-benzyl-piperazine, respectively.

Sources & evidence

ORD record: ord-66acb35fb24d416db0966a667e8062a5
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655632B2

Reaction notes

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