Cesium carbonate → HCID 67620037, compound

HRID 2293348Notes

Reaction equation

HRID 2293348 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:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=1)=[O:34]>C(#N)C>[CH:36]1[C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:43]=[CH:44][C:35]=1[C:33](=[O:34])[CH2:32][N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([N:16]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])=[O:5]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 691792-Bromo-2'-acetonaphthoneHCID 86751513HCID 86751513, compound

Product 1

HCID 67620037HCID 67620037, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure described in example 5, treatment of L-proline-L-isoleucine benzylamide (296 mg, 0.93 mmol), with cesium carbonate (0.61 g, 1.87 mmol), and 2-bromo-2'-acetonaphthone (697 mg, 2.80 mmol, 3.0 eq) in acetonitrile (12 mL), provided 364 mg (80%) of L-isoleucine, N-[1-(2-naphth-2-yl-2-oxoethyl)-L-prolyl] benzylamide as a pale yellow oil.

Sources & evidence

ORD record
ord-cd6ea2ec42294b9b949e551173051bf5
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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