Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester → HCID 86729442, compound

HRID 1507015Notes

Reaction equation

HRID 1507015 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[N+](C1C=C(S(O[CH2:23][C@@H:24]2[CH2:26][O:25]2)(=O)=O)C=CC=1)([O-])=O.[F-].[K+]>C1COCC1>[O:25]1[CH2:26][C@H:24]1[CH2:23][N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1

Participants

5

Reactant 3

HCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 422478IsoindolineHCID 522689Potassium Fluoride

Product 1

HCID 86729442HCID 86729442, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of isoindoline (500 mg, 4.20 mmol) and (S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (1.27 g, 5.04 mmol) in THF (100 mL) was added KF (580 mg, 10 mmol) at 0° C. The reaction mixture was warmed to 25° C., stirred for 16 h, filtered and concentrated. The crude product was used in the next step without further purification. (600 mg, yield 68%) MS (ESI+) e/z: 176.1 [M+1]+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-5b1c13321e8148d0b9abfec2bc8b21a6
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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