p-Toluenesulfonic acid → (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate

HRID 1771159

반응식

HRID 1771159 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][OH:18])[CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:16]=[C:14]1[O:18][CH2:17][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13]1

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 13340758(R)-3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoic acid2회

생성물 1

HCID 697924(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate수율 88.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

(R)-3-(Benzyloxycarbonylamino)-4-hydroxybutanoic acid (INTERMEDIATE 2, 27.7 g, 109.38 mmol) was dissolved in toluene (648 ml). p-Toluenesulfonic acid (367 mg, 2.13 mmol) was added to the solution and the resulting mixture was heated at reflux under Dean-Stark conditions for 3 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. Diethyl ether (200 ml) was added, and formation of crystals was observed upon standing. The crystals were filtered in vacuo. The mother liquors were concentrated in vacuo and additional diethyl ether (40 ml) was added. More crystals appeared which were filtered in vacuo. Both sets of crystals combined to give the title product (22.8 g, yield: 83%).

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux under Dean-Stark conditions for 3 hours
  3. concentrationconcentrated in vacuo
  4. additionDiethyl ether (200 ml) was added
  5. filtrationThe crystals were filtered in vacuo
  6. concentrationThe mother liquors were concentrated in vacuo and additional diethyl ether (40 ml)
  7. additionwas added
  8. filtrationwere filtered in vacuo

출처 및 근거

ORD 기록
ord-faeee7130fe84da088a14db7b1d278ad
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09248140B2

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