Phenacyl bromide → L-isoleucine, N-[1-(2-phenyl-2-oxoethyl)-L-prolyl] benzylamide

HRID 2293347Notes

Reaction equation

HRID 2293347 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH2:9]([NH:16][C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]>C(#N)C>[C:35]1([C:33](=[O:34])[CH2:32][N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([N:16]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])=[O:5])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 10796Cesium carbonateHCID 86751513HCID 86751513, compound

Product 1

HCID 67621189L-isoleucine, N-[1-(2-phenyl-2-oxoethyl)-L-prolyl] benzylamideYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure described in example 5, treatment of L-proline-L-isoleucine benzylamide (361 mg, 1.14 mmol), with cesium carbonate (0.74 g, 2.28 mmol), and 2-bromoacetophenone (1.134 g, 5.69 mmol, 5.0 eq) in acetonitrile (12 mL), provided 466 mg (94%) of L-isoleucine, N-[1-(2-phenyl-2-oxoethyl)-L-prolyl] benzylamide as a pale yellow oil.

Sources & evidence

ORD record
ord-1807b6b7496a4fdf8004b42137c63c44
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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