HCID 69223435, compound → HCID 69224175, compound

HRID 2117266Notes

Reaction equation

[O:1]=[C:2]1[C:8](=[CH:9][O:10]CCO[Si](C)(C)C)[C:7](=[O:18])[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[CH:4][N:3]1[CH2:25][C:26]([N:28]([CH:37]([CH3:39])[CH3:38])[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[O:27]>FC(F)(F)C(O)=O>[O:1]=[C:2]1[C:8](=[CH:9][OH:10])[C:7](=[O:18])[N:6]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:5]=[CH:4][N:3]1[CH2:25][C:26]([N:28]([CH:37]([CH3:39])[CH3:38])[C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)=[O:27]

Participants

Conditions

Temperature: 2.5 °C

Procedure

2-[2,4-Dioxo-5-phenyl-3-[2-(trimethylsilyloxy)-1-ethoxymethylene]-2,3,4,5-tetrahydro-1H-1,5-diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide (12q) was combined with trifluoroacetic acid (10 mL) under argon and cooled to 0-5° C. After approximately 20 min., the reaction mixture was evaporated in vacuo. The residue was triturated with diethyl ether and hexane, filtered and dried under high vacuum to provide 2-[2,4-dioxo-3-(hydroxymethylene)-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide (12r, 0.927 g) as a solid. 1H NMR (400 MHz, CDCl3) 0.91 (d, J=2, 3H), 0.92 (d, J=2, 3H), 3.63 (m, 1H), 3.80 (s, 3H), 3.81 (d, J=17 Hz, 1H), 3.96 (d, J=17 Hz, 1H), 4.17 (dd, J=7, 12 Hz, 1H), 4.29 (dd, J=7, 12 Hz; 1H), 4.92 (m, 1H), 5.89 (d, J=6 Hz, 1H), 5.95 (d, J=6 Hz, 1H), 6.92 (m, 2H), 7.09 (m, 2H), 7.27 (m, 3H), 7.37 (m, 2H). MS (ESI) [M+Na]+=460

Workup

customthe reaction mixture was evaporated in vacuo
customThe residue was triturated with diethyl ether and hexane
filtrationfiltered
customdried under high vacuum

Sources & evidence

ORD record: ord-8bce94a8e26145f1989564b125f5f0bd
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442693B2

Reaction notes

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