5-Bromo-2-furanecarboxylic acid → HCID 59268848, compound

HRID 889069Notes

Reaction equation

HRID 889069 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.Cl.[CH2:11]([O:13][C:14](=[O:24])[C@H:15]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH2:16])[CH3:12]>>[CH2:11]([O:13][C:14](=[O:24])[C@@H:15]([NH:16][C:7]([C:5]1[O:6][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:9])[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:12]

Participants

3

Reactant 2

HCID 685115-Bromo-2-furanecarboxylic acidHCID 73960Glutamic acid diethyl ester hydrochloride

Product 1

HCID 59268848HCID 59268848, compoundYield 72%

Procedure

AAG154489 was synthesized as shown in Scheme 3. Compounds 10 was obtained by a Sonogashira coupling of 5a (from scheme 1) with (S)-2-[(5-bromo-furan-2-carbonyl)-amino]-pentanedioic acid diethyl ester 13. Compound 13 (Scheme 3) was synthesized by coupling the commercially available 5-bromo-2-furan-carboxylic acid 12 and L-glutamate diethyl ester hydrochloride in 72% yield. Hydrogenation and saponification of 10 afforded AAG154489.

Sources & evidence

ORD record
ord-acb51f3ccaf4410c8e1f76fe77063ed3
Source dataset
uspto-grants-2012_08
Patent number
US08252804B2

Reaction notes

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