Sodium Carbonate → HCID 67619690, compound

HRID 2293356Notes

Reaction equation

HRID 2293356 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[CH:32]([CH3:41])[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]>CO>[CH3:41][CH: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])[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 164522-BromopropiophenoneHCID 86751513HCID 86751513, compound

Product 1

HCID 67619690HCID 67619690, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the procedure described in example 5, treatment of L-proline-L-isoleucine benzylamide (196 mg, 0.62 mmol), with sodium carbonate (85 mg, 0.80 mmol), and 2-bromopropiophenone (210 mg, 0.98 mmol, 1.6 eq) in MeOH (12 mL), provided 72 mg (26%) of L-isoleucine, N-[1-(1-methyl-2-phenyl-2-oxoethyl)-L-prolyl] benzylamide.

Sources & evidence

ORD record
ord-ba36dab685b94bdc9445b762602f6c91
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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