Benzyloxycarbonylglycine → 4-[(4-(3-[(S)-2,5-Diaminopentanoylamino]propoxy)-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

HRID 1869006Notes

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][NH2:41])=[CH:33][C:32]=2C)=[C:28]([CH:43]([CH3:45])[CH3:44])[NH:27][N:26]=1)(=O)C.C(OC([NH:56][C@@H:57]([CH2:61][CH2:62][CH2:63][NH:64]C(OCC1C=CC=CC=1)=O)[C:58](O)=[O:59])=O)C1C=CC=CC=1.[CH2:75](OC(NCC(O)=O)=O)C1C=CC=CC=1>>[NH2:56][C@@H:57]([CH2:61][CH2:62][CH2:63][NH2:64])[C:58]([NH:41][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]([CH3:75])[CH:33]=1)=[O:59]

Participants

Reactant 3

HCID 14349Benzyloxycarbonylglycine

HCID 7073470N2,N5-Bis((phenylmethoxy)carbonyl)-L-ornithine

HCID 689401203-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-{[4-(3-aminopropoxy)-2-methylphenyl]-methyl}-5-isopropyl-1H-pyrazole

Product 1

HCID 689466974-[(4-(3-[(S)-2,5-Diaminopentanoylamino]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 13 using 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-aminopropoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole and (S)-2,5-bis-(benzyloxycarbonylamino)pentanoic acid 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-812de80cc81349219c5d6c4fbb1a387c
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635684B2

Reaction notes

Loading…