2-Bromoacetamide → tert-butyl(3R)-3-(3-{[(2-amino-2-oxoethyl)(methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)-6-cyclohexylhexanoate

HRID 1350247Notes

Reaction equation

HRID 1350247 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24][NH:25][CH3:26])[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:28][C:29]([NH2:31])=[O:30]>CCN(CC)CC>[NH2:31][C:29](=[O:30])[CH2:28][N:25]([CH2:24][C:21]1[N:20]=[C:19]([C@H:10]([CH2:9][CH2:8][CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:11][C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[O:23][N:22]=1)[CH3:26]

Participants

4

Reactant 2

HCID 696322-BromoacetamideHCID 16747948tert-butyl(3R)-6-cyclohexyl-3-{3-[(methylamino)methyl]-1,2,4-oxadiazol-5-yl}hexanoate

Product 1

HCID 60077632tert-butyl(3R)-3-(3-{[(2-amino-2-oxoethyl)(methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)-6-cyclohexylhexanoateYield 104.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Method as for preparation 106 using tert-butyl(3R)-6-cyclohexyl-3-{3-[(methylamino)methyl]-1,2,4-oxadiazol-5-yl}hexanoate (preparation 5) (244 mg, 0.67 mmol) and 2-bromoacetamide (95 mg, 0.69 mmol) as starting materials and Et3N as the base to afford the title compound as a colourless oil (296 mg).

Sources & evidence

ORD record
ord-4592b36923e54f69a499e79092655ffb
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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