Sodium Carbonate → L-isoleucine, N-[1-(2-(5-chloro-3-methyl-benzo[B]thiophene-2-yl)-2-oxoethyl)-L-prolyl] benzylamide

HRID 2293351Notes

Reaction equation

HRID 2293351 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+].Cl[CH2:32][C:33]([C:35]1[S:39][C:38]2[CH:40]=[CH:41][C:42]([Cl:44])=[CH:43][C:37]=2[C:36]=1[CH3:45])=[O:34]>C(#N)C>[Cl:44][C:42]1[CH:41]=[CH:40][C:38]2[S:39][C:35]([C:33](=[O:34])[CH2:32][N:1]3[CH2:8][CH2:7][CH2:6][C@H:2]3[C:3]([N:16]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])=[O:5])=[C:36]([CH3:45])[C:37]=2[CH:43]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27798882-Chloro-1-(5-chloro-3-methylbenzo[b]thiophen-2-yl)ethan-1-oneHCID 86751513HCID 86751513, compound

Product 1

HCID 67620542L-isoleucine, N-[1-(2-(5-chloro-3-methyl-benzo[B]thiophene-2-yl)-2-oxoethyl)-L-prolyl] benzylamideYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure described in example 5, treatment of L-proline-L-isoleucine benzylamide (200 mg, 0.63 mmol), with sodium carbonate (100 mg, 0.94 mmol), and 2-chloroacetyl-5-chloro-3-methylbenzo[B]thiophene (Ryan Scientific; Columbia, S.C.: 244 mg, 0.941 mmol, 1.5 eq) in acetonitrile (10 mL), provided 170 mg (50%) of L-isoleucine, N-[1-(2-(5-chloro-3-methyl-benzo[B]thiophene-2-yl)-2-oxoethyl)-L-prolyl] benzylamide as a pale yellow oil that formed a waxy solid on standing.

Sources & evidence

ORD record
ord-3d048b290c5648d29a4b8250840de20f
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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