D-Leucine, methyl ester → (R)-methyl 2-(2,3-dimethylfuran-5-carboxamido)-4-methylpentanoate

HRID 1453486Notes

Reaction equation

HRID 1453486 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=O)[O:5][C:6]=1[CH3:7].[CH3:11][O:12][C:13](=[O:20])[C@@H:14]([CH2:16][CH:17]([CH3:19])[CH3:18])[NH2:15]>>[CH3:7][C:6]1[O:5][C:4]([C:8]([NH:15][C@H:14]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([O:12][CH3:11])=[O:20])=[O:10])=[CH:3][C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 89967D-Leucine, methyl esterHCID 27749244,5-Dimethylfuran-2-carboxylic acid

Product 1

HCID 57527841(R)-methyl 2-(2,3-dimethylfuran-5-carboxamido)-4-methylpentanoateYield 27%

Procedure

Prepared in a similar manner to example 4 using 4,5-dimethyl-furan-2-carboxylic acid and D-leucine methyl ester. Yield: 27%. 1H NMR (500 MHz, CDCl3): δ 0.96 (t, 6H), 1.66 (m, 3H), 1.96 (s, 3H), 2.26 (s, 3H), 3.75 (s, 3H), 4.78 (m, 1H), 6.51 (d, 1H), 6.89 (s, 1H). MS (M+H, 268).

Sources & evidence

ORD record
ord-261ac68051e640dc93f79867e8781cf4
Source dataset
uspto-grants-2009_01
Patent number
US07476399B2

Reaction notes

Loading…