Tert-butyl 2-[4-[3-[(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)amino]-2-methyl-3-oxopropyl]phenoxy]acetate → (+)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8-yl)propyl]phenoxy]acetic acid, ethyl ester

HRID 248084Notes

Reaction equation

[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[C:3]=1[NH:16][C:17](=O)[CH:18]([CH3:35])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([O:30][C:31]([CH3:34])(C)C)=[O:29])=[CH:22][CH:21]=1>C1C=CC=CC=1>[CH2:12]([N:5]1[C:4](=[O:15])[C:3]2[N:16]=[C:17]([CH:18]([CH3:35])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([O:30][CH2:31][CH3:34])=[O:29])=[CH:22][CH:21]=3)[NH:1][C:2]=2[N:7]([CH2:8][CH2:9][CH3:10])[C:6]1=[O:11])[CH2:13][CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve the ethyl enolate of (-)-2-[[4-[3-[(6-amino-1-propyl-1,2,3,4-tetrahydro-3-propyl-2,4-dioxo-5-pyrimidinyl)amino]-2-methyl-3-oxopropyl]phenyl]oxy]-acetic acid, 1,1-dimethylethyl ester (1.01 g, 1.9 mmol) in anhydrous benzene (200 mL) and heat at 80° C. for 24 hours. Evaporate the solvent in vacuo and purify the residue by radial chromatography (40→50% ethyl acetate/hexane) to give (-)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8- yl)propyl]phenoxy]acetic acid, ethyl ester (0.7 g, 81%); [α]d 20 =-54.3° (C=0.856, CHCl3).

Workup

customEvaporate the solvent in vacuo
custompurify the residue by radial chromatography (40→50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-1174c511c5a048268a98e34af184cc4e
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05208240

Reaction notes

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