Triphenylphosphine → HCID 59485912, compound

HRID 1972270Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[C@H:11]([CH2:21]O)[O:10][C:9]2=[O:23])=[CH:4][CH:3]=1.[C:24]1([C:30]2[NH:34][N:33]=[N:32][N:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[C@H:11]([CH2:21][N:32]3[N:33]=[N:34][C:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:31]3)[O:10][C:9]2=[O:23])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(4S,5R)-3-(4-Chlorophenyl)-5-(hydroxymethyl)-4-(3-methoxyphenyl)oxazolidin-2-one (40 mg, 0.12 mmol) and phenyltetrazole (17 mg, 0.12 mmol) are dissolved in DCM (1 mL), cooled to 0° C. and are then subsequently treated with triphenylphosphine (29 mg, 0.11 mmol) and diisopropylazodicarboxylate (0.024 mL, 0.12 mmol). The mixture is allowed to stir to room temperature overnight and is then purified by flash chromatography (4 g Redisep cartridge, 10-30% Ethyl acetate-hexanes) to give the title compound. 1H NMR (acetone-d6, 400 MHz) δ 8.05-8.03 (m, 2H), 7.54-7.50 (m, 3H), 7.47-7.43 (m, 2H), 7.32 (t, J=7.9 Hz, 1H), 7.30-7.24 (m, 2H), 7.09 (t, J=2.08 Hz, 1H), 7.05-7.03 (app d, J=7.8 Hz, 1H), 6.90 (ddd, J=8.3, 2.6, 0.9 Hz, 1H), 5.72 (d, J=5.1 Hz, 1H), 5.50 (dd, J=14.7, 8.7 Hz, 1H), 5.43 (dd, J=14.7, 10.6 Hz, 1H), 5.12-5.08 (m, 1H), 3.76 (s, 3H); HPLC-MS calculated C24H20ClN5O3 (M+H+) 462.1, found 462.1.

Workup

customis then purified by flash chromatography (4 g Redisep cartridge, 10-30% Ethyl acetate-hexanes)

Sources & evidence

ORD record: ord-597cb75280ec486a9fe67faed51f46aa
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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