tert-Butanol → HCID 123831591, compound

HRID 1056879Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10](=[O:30])[CH:11]=[C:12](C(O)=O)[N:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:33]([CH:37](C)C)C(C)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:47])=CC=1.[CH3:57][C:58]([OH:61])([CH3:60])[CH3:59]>>[C:58]([O:61][C:37](=[O:47])[NH:33][C:12]1[N:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10](=[O:30])[CH:11]=1)([CH3:60])([CH3:59])[CH3:57]

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 81531Diisopropylethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 67405349HCID 67405349, compound

Product 1

HCID 123831591HCID 123831591, compound

Conditions

Temperature: 80 °C

Procedure

5-(Benzyloxy)-1-(biphenyl-3-yl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid (48.0 g, 121 mmol), DIPEA (31.25 g, 242 mmol), and DPPA (49.9 g, 91.2 mmol) were added to t-BuOH (500 mL) at room temperature. The resulting solution was heated to at 80° C. for 16 h. After cooling to room temperature, the mixture was concentrated to give a residue which was purified by silica gel chromatography to afford tert-butyl[5-(benzyloxy)-1-(biphenyl-3-yl)-4-oxo-1,4-dihydropyridin-2-yl]carbamate. !H NMR δ (400 MHz, CDCl3): 7.70 (d, J−7.6 Hz, 1H), 7.58-7.53 (m, 3H), 7.47 (m, 2H), 7.42-7.37 (m, 4H), 7.33-7.20 (m, 3H)1 7.18 (d, J=7.2 Hz, 1H), 6.94 (s, 1H), 6.87 (s, 1H), 6.09 (s, 1H), 5.12 (s, 2H)f 1.34 (s, 9H). MS (ESI) (M+H)+ 469.

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated
customto give a residue which
customwas purified by silica gel chromatography

Sources & evidence

ORD record: ord-621f1397b4ff441d984764fcf4921905
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399651B2

Reaction notes

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