Sodium Carbonate → HCID 67620061, compound

HRID 2293350Notes

Reaction equation

HRID 2293350 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][CH:38]=[CH:37][C:36]=1[O:41][CH3:42])=[O:34]>C(#N)C>[CH3:42][O:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[C:33](=[O:34])[CH2:32][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]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123440Bromomethyl 2-methoxyphenyl ketoneHCID 86751513HCID 86751513, compound

Product 1

HCID 67620061HCID 67620061, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure described in example 5, treatment of L-proline-L-isoleucine benzylamide (317 mg, 0.99 mmol), with sodium carbonate (211 mg, 1.99 mmol), and 2-bromo-2'-methoxyacetophenone (457 mg, 1.99 mmol, 2.0 eq) in acetonitrile (10 mL), provided 410 mg (88%) of L-isoleucine, N-[1-(2-(2-methoxyphenyl)-2-oxoethyl)-L-prolyl] benzylamide as a pale yellow oil.

Sources & evidence

ORD record
ord-f6a0e900194f44a48840d47199d50071
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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