Bromomethyl 4-methoxyphenyl ketone → HCID 67621352, compound

HRID 2293354Notes

Reaction equation

HRID 2293354 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]([O:41][CH3:42])=[CH:37][CH:36]=1)=[O:34]>CO>[CH3:42][O: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 4965Bromomethyl 4-methoxyphenyl ketoneHCID 10340Sodium CarbonateHCID 86751513HCID 86751513, compound

Product 1

HCID 67621352HCID 67621352, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the procedure described in example 5, treatment of L-proline-L-isoleucine benzylamide (208 mg, 0.65 mmol), with sodium carbonate (104 mg, 0.98 mmol), and 2-bromo-4'- methoxyacetophenone (195 mg, 0.85 mmol, 1.3 eq) in MeOH (10 mL), provided 248 mg (81%) of L-isoleucine, N-[1-(2-(4-methoxyphenyl)-2-oxoethyl)-L-prolyl] benzylamide as a pale yellow oil.

Sources & evidence

ORD record
ord-0165b76f40f94ee78cd0c6a628ddfbe6
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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