2-Furancarboxylic acid → HCID 67619614, compound

HRID 2293369Notes

Reaction equation

HRID 2293369 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.[CH2:25](N(CC)CC)C.[O:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37]([OH:39])=O>C1COCC1>[O:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37](=[O:39])[CH2:25][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 69192-Furancarboxylic acidHCID 8471TriethylamineHCID 86751513HCID 86751513, compound

Product 1

HCID 67619614HCID 67619614, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, a solution of L-proline-L-isoleucine benzylamide (114 mg, 0.36 mmol), and triethylamine (0.10 mL, 0.78 mmol, 2.0 eq), in THF (10 mL), was treated with 255 mg (1.76 mmol, 5.0 eq) of 2-(alpha-chloroacyl)furan (prepared from 2-furoic acid, using the procedure described in example 1) to provide 130 mg, (85%) of L-isoleucine, N-[1-(2-furan-2-yl-2-oxoethyl)-L-prolyl] benzylamide.

Sources & evidence

ORD record
ord-49548f9bacee4369bd110ec794fdcf33
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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