Sodium Carbonate → HCID 67621198, compound

HRID 2293349Notes

Reaction equation

HRID 2293349 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-].[Na+].[Na+].Br[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:37][CH:36]=1)=[O:34]>C(#N)C>[C:38]1([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:37]=[CH:36][C:35]([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]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 672821-(1,1'-Biphenyl)-4-yl-2-bromoethanoneHCID 86751513HCID 86751513, compound

Product 1

HCID 67621198HCID 67621198, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure described in example 5, treatment of L-proline-L-isoleucine benzylamide (300 mg, 0.95 mmol), with sodium carbonate (200 mg, 1.89 mmol), and 2-bromo-4'-phenylacetophenone (520 mg, 1.89 mmol, 2.0 eq) in acetonitrile (10 mL), provided 484 mg (87%) of L-isoleucine, N-[1-(2-(biphenyl-4-yl)-2-oxoethyl)-L-prolyl] benzylamide as a colorless oil.

Sources & evidence

ORD record
ord-da01096b196f4325a6f4661dcee61ab9
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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