Diisopropylethylamine → HCID 58432115, 화합물

HRID 56525노트

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HRID 56525 반응식
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

참가 물질

7

반응물 2

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

생성물 1

HCID 58432115HCID 58432115, 화합물수율 75.1%

시약·촉매·용매 4

HCID 313Hydrochloric Acid용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b17688f7de674056af790b2014f1eb52
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434707B2

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