Thiophenol → HCID 59486019, compound

HRID 1972205Notes

Reaction equation

CS(O[CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[C@H:8]1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1)(=O)=O.[C:34]1([SH:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:16]2[CH:17]=[CH:18][C:13]([N:9]3[C@@H:8]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=4)[C@H:7]([CH2:6][S:40][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[O:11][C:10]3=[O:12])=[CH:14][CH:15]=2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 75 °C

Procedure

((4S,5R)-3-(4-(4-chlorophenoxy)phenyl)-4-(3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate (0.3 mmol, prepared by the methods described in example 34) was dissolved in ethanol (1.5 mL) and treated with benzenethiol (0.6 mmol) and triethylamine (0.6 mmol). The reaction mixture was heated to 75° C. for 8 h, then was cooled to room temperature, diluted with ethyl acetate, washed with 1M HCl and then purified on silica gel (10-30% ethyl acetate/hexanes) to give the title compound as a colorless oil. 1H NMR (CDCl3) δ (ppm) 7.31-7.37 (m, 5H), 7.24-7.29 (m, 5H), 7.08 (d, 1H, J=7.7 Hz), 6.97-7.04 (m, 2H), 6.86-6.91 (m, 4H), 5.21 (d, 1H, J=4.0 Hz), (ddd, 1H, J=8.4, 4.0, 4.0 Hz), 3.46 (dd, 1H, J=14.2, 3.9 Hz), 3.22 (dd, 1H, J=14.2, 8.7 Hz). HPLC-MS calculated C28H21ClFNO3S (M+H+): 506.1, found 506.1.

Workup

temperaturewas cooled to room temperature
washwashed with 1M HCl
custompurified on silica gel (10-30% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-6466d054443b405e9323a2f5b6e631eb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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