(S)-2-amino-6-(benzyloxycarbonylamino)hexanamide → 4-[(4-{3-[(S)-5-Benzyloxycarbonylamino-1-(carbamoyl)pentylamino]propoxy}-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

HRID 2189386Notes

Reaction equation

HRID 2189386 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]O)=[CH:33][C:32]=2[CH3:42])=[C:28]([CH:43]([CH3:45])[CH3:44])[NH:27][N:26]=1)(=O)C.[NH2:46][C@@H:47]([CH2:51][CH2:52][CH2:53][CH2:54][NH:55][C:56]([O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)=[O:57])[C:48]([NH2:50])=[O:49].NC(C)(C)C(NCCO)=O>>[CH2:59]([O:58][C:56]([NH:55][CH2:54][CH2:53][CH2:52][CH2:51][C@H:47]([NH:46][CH2:40][CH2:39][CH2:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][C:29]2[C:25]([O:24][C@@H:6]3[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]3[OH:4])=[N:26][NH:27][C:28]=2[CH:43]([CH3:44])[CH3:45])=[C:32]([CH3:42])[CH:33]=1)[C:48](=[O:49])[NH2:50])=[O:57])[C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1

Participants

4

Reactant 3

HCID 5326312(S)-2-amino-6-(benzyloxycarbonylamino)hexanamideHCID 216527992-(2-Amino-2-methylpropionylamino)ethanolHCID 689406463-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)-2-methylphenyl]-methyl}-5-isopropyl-1H-pyrazole

Product 1

HCID 689410364-[(4-{3-[(S)-5-Benzyloxycarbonylamino-1-(carbamoyl)pentylamino]propoxy}-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Example 72 using 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole and (S)-2-amino-6-(benzyloxycarbonylamino)hexanamide instead of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole and 2-[2-amino-2-(methyl)propionylamino]ethanol, respectively.

Sources & evidence

ORD record
ord-1817e80cd8594f3191adc44c186e8fd1
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

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