Reaction #42602

ord-fae096518adf4383850e949213f47cf8

Reaction equation

CCCC1CCC(CC(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(CC)c2)CC1=O
N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-2-(3-oxo-4-propylcyclohexyl)acetamide
O=C(O)CC1CCCC(=O)C1
(3-Oxo-cyclohexyl)-acetic acid
→
CCc1cccc(CNC[C@@H](O)[C@H](Cc2cc(F)cc(F)c2)NC(=O)CC2CCCC(=O)C2)c1
N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-2-(3-oxocyclohexyl)acetamide
Yield 23.0%

Reactants

CCCC1CCC(CC(=O)N[C@@H](Cc2cc(F)cc(F)c2)[C@H](O)CNCc2cccc(CC)c2)CC1=O
N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-2-(3-oxo-4-propylcyclohexyl)acetamide
O=C(O)CC1CCCC(=O)C1
(3-Oxo-cyclohexyl)-acetic acid

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-2-(3-oxocyclohexyl)acetamide was prepared in 23% yield from (3-Oxo-cyclohexyl)-acetic acid by the method described for the synthesis of N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-2-(3-oxo-4-propylcyclohexyl)acetamide (EXAMPLE SP-297.)

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07727997B2uspto-grants-2010_06