Hydrochloric Acid → HCID 178525985, compound

HRID 1364373Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of methyl-4-(1,5-dibenzyl-1,2-dihydro-2-oxopyridin-3-yl)-2-hydroxy-4-oxobut-2-enoate 7 (0.069 g, 0.17 mmol) in MeOH (5 mL) at 0° C. was added a solution of 1N NaOH (0.5 mL) and reaction mixture allowed to stir at 0° C. for 30 min. Reaction was then allowed to stir at ambient temperature for 1 h. The reaction mixture was neutralized with 1 N HCl, the solid separated was filtered and dried under vacuum. Recrystallization with EtOAc/Hexane gave yellow solid. Yield 0.034 g (52%), yellow solid, mp 158-159° C. 1H NMR (CDCl3, 500 MHz): δ 3.82 (s, 2H, CH2), 5.26 (s, 2H, CH2), 7.16-7.39 (m, 10H, Ar—H), 7.45 (d, 1H, CH, J=2 Hz), 7.98 (s, 1H, olefenic CH), 8.26 (d, 1H, CH, J=2 Hz), 13C NMR (CDCl3, 125 MHz): δ 37.5, 53.3, 100.8, 119.8, 123.1, 127.0, 128.2, 128.5, 128.5, 128.6, 128.6, 128.9, 128.9, 129.0, 129.1, 129.1, 135.2, 138.4, 141.3, 145.1, 159.5, 162.3, 173.7; HRMS (M+H)+ calcd for C23H20NO5 390.1341, found 390.1342.

Workup

customReaction
stirringto stir at ambient temperature for 1 h
customthe solid separated
filtrationwas filtered
customdried under vacuum
customRecrystallization with EtOAc/Hexane
customgave yellow solid

Sources & evidence

ORD record: ord-bdc58d70ebec406eaded270922357373
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888375B2

Reaction notes

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