Triphenylphosphine → HCID 68069234, compound

HRID 1184507Notes

Reaction equation

[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][CH:7]([CH3:11])[C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.O[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:11][CH:7]1[O:6][C:5]2[CH:12]=[CH:13][C:2]([O:1][CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)=[CH:3][C:4]=2[NH:9][C:8]1=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 40 mL vial, 6-hydroxy-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one 394C (0.200 g, 1.116 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (0.225 g, 1.116 mmol), and PPh3 (0.439 g, 1.674 mmol) were suspended in THF (5.58 mL) to give a brown solution. The mixture was cooled to 0° C. To the cooled mixture was added DEAD drop-wise. The reaction was slowly warmed to 23° C. and stirred for 18 hr. The crude material was purified by prep HPLC-MS (45-85% MeCN in water). The fractions were collected and concentrated in vacuo to give the title compound (0.223 g, 55.1% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33-1.44 (m, 9H) 1.44-1.59 (m, 2H) 1.86 (ddd, J=9.47, 6.32, 3.16 Hz, 2H) 3.06-3.24 (m, 2H) 3.33-3.71 (m, 5H) 4.32-4.44 (m, 1H) 4.57 (q, J=6.65 Hz, 1H) 6.48 (d, J=2.78 Hz, 1H) 6.55 (dd, J=8.84, 2.78 Hz, 1H) 6.86 (d, J=8.59 Hz, 1H) 10.56 (s, 1H). ESI-MS: m/z 307.2 and 263.2 (M+H)+.

Workup

customto give a brown solution
temperatureThe reaction was slowly warmed to 23° C.
customThe crude material was purified by prep HPLC-MS (45-85% MeCN in water)
customThe fractions were collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-60287fb3fd6f4f7980348f1694ce6158
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669249B2

Reaction notes

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