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Triethylamine → (R)-2-(((Benzyloxy)carbonyl)amino)pentane-1,5-diyl dimethanesulfonate

HRID 1180978
ノート
印刷プレビュー

反応式

HRID 1180978 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][C@@H:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][OH:7].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:26][S:27]([O:7][CH2:6][C@H:5]([NH:8][C:9]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:18])[CH2:4][CH2:3][CH2:2][O:1][S:27]([CH3:26])(=[O:29])=[O:28])(=[O:29])=[O:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2757382(R)-Benzyl (1,5-dihydroxypentan-2-yl)carbamate

生成物 1

HCID 66524788(R)-2-(((Benzyloxy)carbonyl)amino)pentane-1,5-diyl dimethanesulfonate

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

A solution of benzyl(1R)-4-hydroxy-1-(hydroxymethyl)butylcarbamate (1.5 g) in DCM (60 ml) was treated with triethylamine (3.3 ml) and stirred at room temperature for 10 min. Methanesulphonyl chloride (1.34 ml) was then added dropwise and the resultant mixture stirred at 0° C. for 75 min. Sodium bicarbonate solution was added and the reaction mixture allowed to reach room temperature over 1 h. The organic layer was separated, washed with brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give a yellow oil. The oil was purified using Biotage™ chromatography (eluting with hexane:ethyl acetate 1:2, 1:3) to give the title compound (1.924 g) as a yellow oil

後処理

  1. waitto reach room temperature over 1 h
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (over magnesium sulphate)
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow oil
  7. customThe oil was purified
  8. washBiotage™ chromatography (eluting with hexane:ethyl acetate 1:2, 1:3)

出典と根拠

ORDレコード
ord-a337d4bfb19944f182aeebcb6f98f997
出典データセット
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07282497B2

反応ノート

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