HCID 10583869, compound → HCID 10687511, compound

HRID 1066025Notes

Reaction equation

[CH2:1]([C@@H:8]1[NH:11][C:10](=[O:12])[C@H:9]1[O:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:15]([C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)=O)C1C=CC=CC=1>>[N:29]1[CH:30]=[CH:31][C:26]([CH2:25][NH:24][C:22]([N:11]2[C@@H:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@H:9]([O:13][CH3:14])[C:10]2=[O:12])=[O:15])=[CH:27][CH:28]=1

Participants

Reactant 2

HCID 10583869HCID 10583869, compound

HCID 10823223HCID 10823223, compound

Product 1

HCID 10687511HCID 10687511, compound

Procedure

Following the same procedure as in example 1 step F, but using 4(S)-benzyl-3(S)-methoxyazetidin-2-one as starting material and 4-{{(phenoxycarbonyl)amino}methyl}pyridine as reactant, 4(S)-benzyl-3(S)-methoxy-2-oxoazetidine-1-carboxylic acid (4-pyridinylmethyl)amide was obtained as a light yellow oil. 1H-NMR (400 MHz, CDCl3) δ8.60-7.22 (m, 9H), 7.06-7.04 (m, 1H), 4.52-4.50 (m, 2H), 4.28 (d, J=2.2 Hz, 1H), 4.21-4.17 (m, 1H), 3.57 (dd, J=14, 3.5 Hz, 1H), 3.15 (s, 3H), 2.93 (dd, J=14.2, 8.9 Hz, 1H); IR (neat) υ1773,1770 cm−1; FAB-MS m/z 329 (MH+); HRMS calcd for C18H20N3O3: 326.1504 (MH+); found: 326.1519.

Sources & evidence

ORD record: ord-61dca0a98fd244a893bcde6abb41c57d
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06242439B1

Reaction notes

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