4-Toluenesulfonyl chloride → HCID 59201644, 화합물

HRID 451882노트

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HRID 451882 반응식
[CH2:1]1[C:3]2([CH2:8][CH2:7][C@H:6]([CH2:9][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][OH:12])[CH2:5][O:4]2)[CH2:2]1.[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH3:28][C:27]1[CH:29]=[CH:30][C:24]([S:21]([O:12][CH2:11][C@@H:10]([NH:13][C:14]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:20])[CH2:9][C@H:6]2[CH2:7][CH2:8][C:3]3([CH2:2][CH2:1]3)[O:4][CH2:5]2)(=[O:23])=[O:22])=[CH:25][CH:26]=1

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 59201744HCID 59201744, 화합물

생성물 1

HCID 59201644HCID 59201644, 화합물

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

The tert-butyl (S)-1-((R)-4-oxaspiro[2.5]oct-6-yl)-3-hydroxypropan-2-ylcarbamate (1.70 g, 5.92 mmol) and tosyl chloride (4.5 g, 23.7 mmol, 4.0 equiv) were dissolved in pyridine (30 mL) and the mixture stirred at room temperature for 17 hr. The pyridine was removed in vacuo and the residue partitioned between EtOAc and 1.0 M HCl. The layers were separated and the organic layer washed with brine, dried over Na2SO4, filtered and evaporated. The (S)-2-(tert-butoxycarbonylamino)-3-((R)-4-oxaspiro[2.5]oct-6-yl)propyl 4-methylbenzenesulfonate was purified by flash chromatography on silica eluting with 0-29% EtOAc in hexanes. The fractions were evaporated and used directly in the next step. MS ESI +ve m/z 464 (M+Na).

후처리

  1. customThe pyridine was removed in vacuo
  2. customthe residue partitioned between EtOAc and 1.0 M HCl
  3. customThe layers were separated
  4. washthe organic layer washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe (S)-2-(tert-butoxycarbonylamino)-3-((R)-4-oxaspiro[2.5]oct-6-yl)propyl 4-methylbenzenesulfonate was purified by flash chromatography on silica eluting with 0-29% EtOAc in hexanes
  9. customThe fractions were evaporated

출처 및 근거

ORD 기록
ord-2d761213fc324b38a807358bcf59f86e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

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