Sodium Carbonate → HCID 67619134, compound

HRID 2293346Notes

Reaction equation

HRID 2293346 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]([O:35][CH3:36])=[O:34]>C(#N)C>[CH3:36][O:35][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 60984Methyl bromoacetateHCID 86751513HCID 86751513, compound

Product 1

HCID 67619134HCID 67619134, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure described in example 5, treatment of L-proline-L-isoleucine benzylamide (47 mg, 0.15 mmol), with sodium carbonate (31 mg, 0.29 mmol, 2.0 eq), and methyl alpha-bromoacetate (113 mg, 0.74 mmol, 5.0 eq) in acetonitrile (5 mL), provided 50 mg (87%) of L-isoleucine, N-[1-(2-methoxy-2-oxoethyl)-L-prolyl] benzylamide as a white foam.

Sources & evidence

ORD record
ord-b1760f66f3e0457d99409b0b00bac3dc
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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