Acetic Acid → HCID 68538687, compound
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]([CH2:37][CH2:38][CH2:39][C:40](=[O:63])[NH:41][C:42]([C:45]([N:47]3[CH2:52][CH2:51][N:50]([C:53]([O:55][CH2:56][C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)=[O:54])[CH2:49][CH2:48]3)=[O:46])([CH3:44])[CH3:43])=[CH:33][CH:32]=2)=[C:28]([CH:64]([CH3:66])[CH3:65])[NH:27][N:26]=1)(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[CH2:56]([O:55][C:53]([N:50]1[CH2:49][CH2:48][N:47]([C:45]([C:42]([NH:41][C:40]([CH2:39][CH2:38][CH2:37][C:34]2[CH:35]=[CH:36][C:31]([CH2:30][C:29]3[C:25]([O:24][C@@H:6]4[O:7][C@H:8]([CH2:19][OH:20])[C@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]4[OH:4])=[N:26][NH:27][C:28]=3[CH:64]([CH3:66])[CH3:65])=[CH:32][CH:33]=2)=[O:63])([CH3:43])[CH3:44])=[O:46])[CH2:52][CH2:51]1)=[O:54])[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-[(4-{3-[1-{[4-(benzyloxycarbonyl)piperazin-1-yl]carbonyl}-1-(methyl)-ethylcarbamoyl]propyl}phenyl)methyl]-5-isopropyl-1H-pyrazole (39.5 g) in methanol (160 mL) was added sodium methoxide (28% methanol solution, 8.24 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added acetic acid (2.7 mL), and the resulting mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (21.3 g).
Workup
- concentrationthe resulting mixture was concentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)
Sources & evidence
- ORD record
- ord-c6ef294ccd434959ac6d10f25b1a9fdd
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375087B2
Reaction notes
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