Water → HCID 59486012, compound

HRID 1972195Notes

Reaction equation

HRID 1972195 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][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]=[CH:20][CH:19]=4)[C@H:16]([CH2:24][OH:25])[O:15][C:14]3=[O:26])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH:29]([N:32]=[C:33]=[O:34])([CH3:31])[CH3:30].O.C(OCC)(=O)C>CN(C=O)C>[CH:29]([NH:32][C:33](=[O:34])[O:25][CH2:24][C@@H:16]1[O:15][C:14](=[O:26])[N:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:28][CH:27]=3)=[CH:12][CH:11]=2)[C@H:17]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 61277Isopropyl isocyanateHCID 24946196HCID 24946196, compound

Product 1

HCID 59486012HCID 59486012, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (4S,5R)-3-(4-(4-chlorophenoxy)phenyl)-5-(hydroxymethyl)-4-phenyloxazolidin-2-one (33 mg, 0.08 mmol) in 0.3 mL DMF was added isopropyl isocyanate (0.015 mL, 0.16 mmol). The reaction was stirred for 3 h at room temperature until reaction completed as judged by TLC. Water and ethyl acetate were added and the phases separated. The organic phase was washed with brine, dried (MgSO4), and concentrated. 13 mg (33%) of the title compound was obtained as a white solid after Prep-LC purification (10-90 Acetonitrile/water (0.05% ammonium acetate). 1H NMR (CDCl3) δ (ppm) 7.30-7.39 (m, 7H), 7.23-7.26 (m, 2H), 6.84-6.90 (m, 4H), 5.14 (d, 1H, J=5.6 Hz), 4.67 (d, 1H, J=7.2 Hz), 4.34-4.53 (m, 3H), 3.77-3.85 (m, 1H), 1.17 (d, 3H, J=6.5 Hz), 1.13 (d. 3H, J=6.5 Hz). HPLC-MS calculated C26H25ClN2O5 (M+H+): 481.2, found: 481.1.

Workup

  1. customthe phases separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3d27a7fc1c234dac8990102c1245eb8e
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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