Lithium Hydroxide → HCID 58305269, compound

HRID 1805350Notes

Reaction equation

HRID 1805350 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([C:19]4[CH:20]=[C:21]([CH:25]=[C:26]([N:28]5[CH2:32][CH2:31][O:30][C:29]5=[O:33])[CH:27]=4)[C:22]([O-:24])=[O:23])[C:11]3=[O:34])[CH2:9]2)=[CH:4][CH:3]=1.[OH-].[Li+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([C:19]4[CH:20]=[C:21]([CH:25]=[C:26]([N:28]5[CH2:32][CH2:31][O:30][C:29]5=[O:33])[CH:27]=4)[C:22]([OH:24])=[O:23])[C:11]3=[O:34])[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86654394HCID 86654394, compound

Product 1

HCID 58305269HCID 58305269, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (1S,2S) and (1R,2R)-3-(2-(4-chlorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)-5-(2-oxooxazolidin-3-yl)benzoate (43 mg, 0.088 mmol) in MeOH (2 mL) and H2O (0.2 mL) was added lithium hydroxide (18 mg, 0.44 mmol). The reaction mixture was stirred at room temperature until TLC indicated no further reaction. The methanol was removed under reduced pressure. After quenching with concentrated HCl (3.0 N), the mixture was extracted with ethyl acetate for three times. The organic layers were dried over anhydrous Na2SO4 and concentrated to give the crude product. Purification by preparative HPLC gave desired product as white solid (29 mg, 70%). LC/MS m/e calcd. for C26H19ClN2O5: 474, observed (M+H)+: 475.1 1H NMR (400 MHz, MeOD-d4) δppm 2.22-2.33 (m, 2 H) 3.35-3.39 (m, 1 H) 4.22 (t, J=8.08 Hz, 2H) 4.56 (t, J=7.96 Hz, 2 H) 6.15 (d, J=7.07 Hz, 1 H) 6.81 (t, J=7.20 Hz, 1 H) 6.96 (d, J=7.83 Hz, 1 H) 7.15 (t, J=7.33 Hz, 1 H) 7.33 (q, J=8.51 Hz, 4 H) 7.91 (s, 1 H) 8.11 (t, J=2.02 Hz, 1 H) 8.26 (s, 1 H).

Workup

  1. customno further reaction
  2. customThe methanol was removed under reduced pressure
  3. customAfter quenching with concentrated HCl (3.0 N)
  4. extractionthe mixture was extracted with ethyl acetate for three times
  5. dry with materialThe organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-9f70fa664d6947e696c59b8a68df2206
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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