Boron tribromide → HCID 59485911, compound

HRID 1972201Notes

Reaction equation

[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=4)[C@H:16]([CH2:26][OH:27])[O:15][C:14]3=[O:28])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=4)[C@H:16]([CH2:26][OH:27])[O:15][C:14]3=[O:28])=[CH:11][CH:12]=2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: -78 °C

Procedure

(4S,5R)-3-(4-(4-chlorophenoxy)phenyl)-5-(hydroxymethyl)-4-(3-methoxyphenyl)oxazolidin-2-one (Example 91) was dissolved in dichlormethane, cooled to −78° C., and treated with boron tribromide (1M solution, 2.1 eq). After 10 min, the cooling bath was removed, and the reaction mixture is stirred for 1 h. The reaction was then quenched with water, extracted with ethyl acetate, dried over magnesium sulfate, filtered, concentrated, and purified on silica gel (2-5% methanol/dichlormethane) to give the title compound. 1H NMR (acetone-d6) δ (ppm) 8.36 (s, 1H), 7.42 (d, J=9.1 Hz, 2H), 7.23 (d, J=9.0 Hz, 2H), 7.09 (t, J=7.9 Hz, 1H), 6.85-6.81 (m, 4H), 6.77 (d, J=7.6 Hz, 1H), 6.74 (m, 1H), 6.67 (dd, J=8.1, 2.4 Hz, 1H), 5.39 (d, J=5.2 Hz, 1H), 4.49 (t, J=5.9 Hz, 1H), 4.36 (ddd, J=5.6, 3.7, 3.4), 3.96 (ddd, J=12.4, 5.7, 3.6 Hz, 1H), 3.85 (ddd, J=12.3, 5.6, 3.8 Hz, 1H); HPLC-MS calculated C22H18ClNO5 (M+H+): 411.1, found: 410.0.

Workup

customthe cooling bath was removed
customThe reaction was then quenched with water
extractionextracted with ethyl acetate
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
custompurified on silica gel (2-5% methanol/dichlormethane)

Sources & evidence

ORD record: ord-8e8b770d20ca4224aa93bc626df2907a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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