4-Toluenesulfonyl chloride → HCID 59201644、化合物

HRID 451882ノート

反応式

HRID 451882 の反応式
[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

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 59201744HCID 59201744、化合物

生成物 1

HCID 59201644HCID 59201644、化合物

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2d761213fc324b38a807358bcf59f86e
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

反応ノート

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