Water → HCID 57752488, 화합물

HRID 225421노트

반응식

HRID 225421 반응식
[CH2:1]([O:8][CH2:9][CH:10]([OH:17])[CH2:11][CH2:12][S:13]([NH2:16])(=[O:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19].O>N1C=CC=CC=1>[CH3:25][C:24]1[CH:26]=[CH:27][C:21]([S:18]([O:17][CH:10]([CH2:11][CH2:12][S:13](=[O:15])(=[O:14])[NH2:16])[CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:20])=[O:19])=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 20355553HCID 20355553, 화합물

생성물 1

HCID 57752488HCID 57752488, 화합물수율 62.9%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of hydroxyl-sulfonamide 5 (77 g, 0.30 mol) in pyridine (730 mL, 9.5 vol) was cooled to <10° C. in a 2 L round bottom flask. Tosyl chloride (56.6 g, 0.30 mol) is added to the solution over 5 minutes maintaining the internal temperature below 10° C. The reaction was allowed to warm to room temperature with stirring overnight. The completed reaction was poured into water (10 vol, 770 mL) to give an orange solution which was extracted with iPrOAc/MTBE (1:1, 2×1.5L). The combined organics were washed with brine (2×500 mL), aqueous HCL (2M, 2×500 mL) then brine (1×500 mL). The organic portion was dried (Na2SO4), filtered and evaporated to give sulfonate 6 as an orange oil (78 g).

후처리

  1. temperaturemaintaining the internal temperature below 10° C
  2. customThe completed reaction
  3. customto give an orange solution which
  4. extractionwas extracted with iPrOAc/MTBE (1:1, 2×1.5L)
  5. washThe combined organics were washed with brine (2×500 mL), aqueous HCL (2M, 2×500 mL)
  6. dry with materialThe organic portion was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-ee73289096ae43ec94e9d671f56063b1
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557095B2

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