Benzyloxycarbonylglycine → 3-(beta-D-Glucopyranosyloxy)-5-isopropyl-4-{[4-(2-{2-methyl-2-[(piperazin-1-yl)carbonyl]propionylamino}ethoxy)-2-methylphenyl]methyl}-1H-pyrazole
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][NH2:40])=[CH:33][C:32]=2[CH3:41])=[C:28]([CH:42]([CH3:44])[CH3:43])[NH:27][N:26]=1)(=O)C.C(OC([N:55]1[CH2:60][CH2:59][N:58]([C:61](=[O:68])[C:62]([C:65](O)=[O:66])([CH3:64])[CH3:63])[CH2:57][CH2:56]1)=O)C1C=CC=CC=1.C(OC(NCC(O)=O)=O)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][NH:40][C:65](=[O:66])[C:62]([CH3:63])([C:61]([N:58]4[CH2:59][CH2:60][NH:55][CH2:56][CH2:57]4)=[O:68])[CH3:64])=[CH:33][C:32]=3[CH3:41])=[C:28]([CH:42]([CH3:44])[CH3:43])[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
4
Reactant 3
Product 1
Procedure
The title compound was prepared in a similar manner to that described in Example 13 using 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(2-aminoethoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole and 1-benzyloxycarbonyl-4-[2-carboxy-2-(methyl)propionyl]piperazine instead of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-aminopropoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole and 2-benzyloxycarbonylaminoacetic acid, respectively.
Sources & evidence
- ORD record
- ord-a62ed2272ad24185b00976fe759ba3ab
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635684B2
Reaction notes
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