HCID 86756759, compound → HCID 86756758, compound
Reaction equation
[CH:1]1([C@H:6]([C:24](=[O:33])[NH:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[C@@H:7]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:8]([NH:10][N:11]([CH2:16][CH:17]([CH3:19])[CH3:18])[S:12]([CH3:15])(=[O:14])=[O:13])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.ONC([C@H]([C@@H](CC(C)C)C(NN(CC(C)C)S(C)(=O)=O)=O)CSC1C=CC=CC=1)=O.CS(C(C=C(C)C)C(NN)=O)(=O)=O.C(N(S(C)(=O)=O)NC(=O)CC=C(C)C)C(C)C>>[CH:1]1([C@H:6]([C:24](=[O:33])[NH:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[C@@H:7]([CH:20]=[C:21]([CH3:23])[CH3:22])[C:8]([NH:10][N:11]([CH2:16][CH:17]([CH3:18])[CH3:19])[S:12]([CH3:15])(=[O:14])=[O:13])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
Procedure
In an analogous manner to that described in the first paragraph of Example 45, starting from 0.357 g of a mixture of 2(R)-[(S)-(cyclopentyl)[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]methyl]-2′-isobutyl-2′-(methanesulphonyl)-4-methylvalerohydrazide and 2(R)-[(S)-(cyclopentyl)[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]methyl]-2′-isobutyl-2′-(methanesulphonyl)-4-methyl-3-pentenohydrazide there was obtained 0.219 g of a mixture of 2(R)-[(S)-(cyclopenyl)(hydroxycarbamoyl)methyl]-2′-isobutyl-2′-(methanesulphonyl-4-methyl-3-pentenohydrazide (compound A) and 2(R)-[(S)-(cyclopentyl)hydroxycarbamoyl)methyl]-2′-isobutyl-2′-(methanesulphonyl)-4-methyl-3-pentenohydrazide (compound B) in the form of a white solid. The compounds were then separated by preparative high-performance liquid chromatography on a DYNAMAX 5 mm C18 300A column with dimensions of 21.4×50 mm using the gradient elution method specified below:
Sources & evidence
- ORD record
- ord-a52aa42697f743a9826104acd5ac0286
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235787B1
Reaction notes
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