Diisopropylethylamine → HCID 58432115, compound

HRID 2359184Notes

Reaction equation

HRID 2359184 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=1)(=[O:7])=[O:6].C(N(CC)C(C)C)(C)C>CN(C=O)C.O.Cl.[Cl-].[Na+].O>[O:6]=[S:5]1(=[O:7])[CH2:4][CH2:3][CH2:2][N:8]1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=1

Participants

7

Reactant 2

HCID 81531DiisopropylethylamineHCID 58432097Methyl 2-(4-(3-chloropropylsulfonamido)phenyl)-2-methoxyacetate

Product 1

HCID 58432115HCID 58432115, compoundYield 75.1%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-(4-(3-chloropropylsulfonamido)phenyl)-2-methoxyacetate (1.03 g, 3.07 mmol) in anhydr DMF (10 mL) was added N,N-diisopropylethylamine (2.0 mL, 11.5 mmol). The mixture was heated at 50° C. under argon for 17 hrs. After cooling to room temperature, the reaction was diluted with H2O, 1 M HCl and brine then extracted with EtOAc. The combined organics were washed with 1 M HCl, H2O and brine the dried over Na2SO4 and concentrated in vacuo. The residue was triturated with Et2O-EtOAc. After sitting overnight, the solution was decanted from solids then concentrated in vacuo. Purification by chromatography (50-70% EtOAc-hexanes) provided methyl 2-(4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)-2-methoxyacetate as an impure oil (0.69 g, 75% yield). The product was used in the next synthetic step without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthen extracted with EtOAc
  3. washThe combined organics were washed with 1 M HCl, H2O and brine the
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with Et2O-EtOAc
  7. customthe solution was decanted from solids
  8. concentrationthen concentrated in vacuo
  9. customPurification by chromatography (50-70% EtOAc-hexanes)

Sources & evidence

ORD record
ord-7ed6f11a14c640c9be797e6b2cbaaf07
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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