Sodium Carbonate → HCID 67619825, compound

HRID 2293352Notes

Reaction equation

HRID 2293352 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]([Cl:41])=[CH:37][CH:36]=1)=[O:34]>CO>[Cl:41][C:38]1[CH:39]=[CH:40][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:36][CH:37]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 68303p-Chlorophenacyl bromideHCID 86751513HCID 86751513, compound

Product 1

HCID 67619825HCID 67619825, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the procedure described in example 5, treatment of L-proline-L-isoleucine benzylamide (182 mg, 0.57 mmol), with sodium carbonate (60 mg, 0.57 mmol), and 2-bromo-4'-chloroacetophenone (147 mg, 0.63 mmol, 1.0 eq), in methanol (10 mL), provided 237 mg (88%) of L-isoleucine, N-[1-(2-(4-chlorophenyl)-2-oxoethyl)-L-prolyl] benzylamide as a pale yellow oil.

Sources & evidence

ORD record
ord-0c98dac6c1b04829ba6254d104571958
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

Loading…