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Water → N,N'-di-Boc-2-methanesulfonyloxy-1,3-diaminopropane

HRID 879967
ノート
印刷プレビュー

反応式

HRID 879967 の反応式
[C:1]([NH:8][CH2:9][CH:10]([OH:20])[CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>C(Cl)Cl>[C:13]([NH:12][CH2:11][CH:10]([O:20][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]
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 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 375632tert-butyl N-{3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}carbamate

生成物 1

HCID 14839452N,N'-di-Boc-2-methanesulfonyloxy-1,3-diaminopropane収率 62%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

To a solution of N,N′-di-Boc-2-hydroxy-1,3-diaminopropane (13.19 g, 45.4 mmol) and triethylamine (1.5 eq, 9.5 ml, 68.1 mmol) in dry 50 ml CH2Cl2 was added dropwise a solution of methanesulfonyl chloride (1.5 eq, 5.25 ml, 68 mmol) in dry 15 ml CH2Cl2 over a period of 1 h at 0° C. with stirring under nitrogen. After the addition, the reaction was stirred overnight at room temperature. Water was slowly added to quench the reaction; the organic layer was separated and then washed with water (5×15 ml) and dried over Na2SO4 and evaporated to give white solid. Recrystallization from hot acetone and cyclohexane gave 10.36 g (62%) white solid. M.p.=127° C.

後処理

  1. additionAfter the addition
  2. stirringthe reaction was stirred overnight at room temperature
  3. customto quench
  4. customthe reaction
  5. customthe organic layer was separated
  6. washwashed with water (5×15 ml)
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customto give white solid
  10. customRecrystallization from hot acetone and cyclohexane

出典と根拠

ORDレコード
ord-0eeceb69d2864ba39f2631a21a1a6e59
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08993544B2

反応ノート

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