Cyclopentylamine → (3R)-N-(benzyloxy)-6-cyclohexyl-3-{4-[(cyclopentylamino)methyl]-1,3-oxazol-2-yl}hexanamide

HRID 2084501Notes

Reaction equation

HRID 2084501 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:29])[CH2:11][C@H:12]([C:22]1[O:23][CH:24]=[C:25]([CH:27]=O)[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH2:1]([O:8][NH:9][C:10](=[O:29])[CH2:11][C@H:12]([C:22]1[O:23][CH:24]=[C:25]([CH2:27][NH:35][CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 60077589(3R)-N-(benzyloxy)-6-cyclohexyl-3-(4-formyl-1,3-oxazol-2-yl)hexanamide

Product 1

HCID 60077641(3R)-N-(benzyloxy)-6-cyclohexyl-3-{4-[(cyclopentylamino)methyl]-1,3-oxazol-2-yl}hexanamideYield 52.2%

Procedure

Method and purification as for preparation 157 using (3R)-N-(benzyloxy)-6-cyclohexyl-3-(4-formyl-1,3-oxazol-2-yl)hexanamide (preparation 156) (200 mg, 0.50 mmol) and cyclopentylamine (50 μl, 0.50 mmol) as starting materials to afford the title compound as a colourless oil (122 mg, 48%).

Workup

  1. customMethod and purification

Sources & evidence

ORD record
ord-7ec4682249fb449c88d0db35bb2073d1
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

Loading…