Diethyl N-(4-aminobenzoyl)-L-glutamate → 2-[4-(Pyrimidin-2-ylamino)-benzoylamino]-pentanedioic acid diethyl ester

HRID 1988071Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([O:10][C:11](=[O:30])[C@H:12]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[NH:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)[CH3:9]>CN(C=O)C>[CH2:8]([O:10][C:11](=[O:30])[CH:12]([NH:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:17][CH:16]=1)[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH3:9]

Participants

Conditions

Temperature: 110 °C

Procedure

2-Chloropyrimidine (0.72 g, 6.3 mmol) and N-(4-aminobenzoyl)-L-glutamic acid diethyl ester (2.04 g, 6.3 mmol, 1 equiv.) were dissolved in DMF (4 mL) and the resulting mixture was heated to 110° C. for 3 hrs. Reaction was complete as determined by TLC. The mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, and concentrated by rotavap. The residue was purified by column chromatography (silica gel, 50% EtOAc/hexane) to afford 1.75 g of desired product 2-[4-(pyrimidin-2-ylamino)-benzoylamino]-pentanedioic acid diethyl ester in 69% yield. MS (ESI) m/z 399.

Workup

customReaction
temperatureThe mixture was cooled to room temperature
custompartitioned between ethyl acetate and water
washThe organic phase was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated by rotavap
customThe residue was purified by column chromatography (silica gel, 50% EtOAc/hexane)

Sources & evidence

ORD record: ord-4842c3e460254e08a16f558392042157
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07553873B2

Reaction notes

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