p-Toluenesulfonic acid monohydrate → (2R,3R)-N-Boc-3-amino-pent-4-yne-2-ol

HRID 366754노트

반응식

HRID 366754 반응식
[C:1]([N:8]1[C@H:12]([C:13]#[CH:14])[C@@H:11]([CH3:15])[O:10]C1(C)C)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([NH:8][C@H:12]([C:13]#[CH:14])[C@H:11]([OH:10])[CH3:15])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12970128275387-85-4

생성물 1

HCID 21971742(2R,3R)-N-Boc-3-amino-pent-4-yne-2-ol수율 83%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of (4R,5R)-N-boc-4-ethynyl-2,2,5-trimethyl-oxazolidine (1.60 g 6.69 mmol) (Example 102B) and p-toluenesulfonic acid monohydrate (130 mg 0.67 mmol) in MeOH (70 mL) was heated at refluxed. After stirring overnight the solvent was concentrated and the residue was chromatographed directly on a silica gel column with a 0-40% EtOAc in hexanes gradient. This afforded the product (Yield 1.10 g, 83%) as well as recovered starting material (220 mg, 14%).

후처리

  1. temperatureat refluxed
  2. concentrationwas concentrated
  3. customthe residue was chromatographed directly on a silica gel column with a 0-40% EtOAc in hexanes gradient

출처 및 근거

ORD 기록
ord-13b645c71ffb4ad4bbec984027e57621
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130239

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