Hydrochloric Acid → HCID 86681692, compound

HRID 571284Notes

Reaction equation

HRID 571284 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([CH2:16][C:17]([O:19]C)=[O:18])[C:9]2=[O:21])(=[O:4])=[O:3].Cl>O1CCOCC1.O>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([CH2:16][C:17]([OH:19])=[O:18])[C:9]2=[O:21])(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86681691HCID 86681691, compound

Product 1

HCID 86681692HCID 86681692, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 2-(5-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (obtained as described in Example 30, Step 3, theoretical amount 1.622 mmol) in dioxane (10 ml), a 36% solution of HCl in water (10 ml) was added, and the mixture was stirred for 3 hours at room temperature. The volatiles were evaporated and the resulting crude was purified by flash chromatography on silica gel (eluent: DCM/MeOH 95:5). The title compound was obtained as a pale yellow solid (230 mg, 0.772 mmol, 47.6% yield over 2 steps, MS/ESI+ 299.1 [MH]+).

Workup

  1. customThe volatiles were evaporated
  2. customthe resulting crude was purified by flash chromatography on silica gel (eluent: DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-5678994861454766b6e79538f6ffd159
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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