Ethyl Acetate → (E)-(7S,10S,13S)-13-tert-Butoxycarbonylamino-10-isopropyl-9,12-dioxo-2-oxa-8,11-diazabicyclo[13.2.2]nonadeca-1(18),4,15(19),16-tetraene-7-carboxylic acid methyl ester

HRID 2371324노트

반응식

HRID 2371324 반응식
[CH3:1][O:2][C:3](=[O:38])[C@@H:4]([NH:8][C:9](=[O:37])[C@@H:10]([NH:14][C:15](=[O:36])[C@@H:16]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25]C=C)=[CH:20][CH:19]=1)[CH:11]([CH3:13])[CH3:12])[CH2:5][CH:6]=[CH2:7].CCOC(C)=O>ClC(Cl)CCl>[CH3:1][O:2][C:3]([C@H:4]1[NH:8][C:9](=[O:37])[C@H:10]([CH:11]([CH3:13])[CH3:12])[NH:14][C:15](=[O:36])[C@@H:16]([NH:28][C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])[CH2:17][C:18]2=[CH:23][CH:22]=[C:21]([CH:20]=[CH:19]2)[O:24][CH2:25][CH:7]=[CH:6][CH2:5]1)=[O:38]

참가 물질

4

반응물 2

HCID 8857Ethyl AcetateHCID 66847339(S)-2-{(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino propionylamino]-3-methylbutyrylamino}-pent-4-enoic acid methyl ester

생성물 1

HCID 66847119(E)-(7S,10S,13S)-13-tert-Butoxycarbonylamino-10-isopropyl-9,12-dioxo-2-oxa-8,11-diazabicyclo[13.2.2]nonadeca-1(18),4,15(19),16-tetraene-7-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 65741,1,2-Trichloroethane용매

실험 절차

Diene 44 (1.80 g, 3.39 mmol) was dissolved in anhydrous 1,1,2-trichloroethane (0.01M) under an atmosphere of argon. GSGC (0.10 equiv) was added. The mixture was heated at reflux for one hour. Two further additions of GSGC (0.10 equiv) were added and after each the reaction mixture was subjected to one h and eighteen h of reflux respectively. This was then cooled and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a brown solid, 0.205 g, 12%. Rf=0.24 (1/1 EtOAc/(50/70) petroleum ether). m.p. 105-107° C.

후처리

  1. additionGSGC (0.10 equiv) was added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for one hour
  4. additionTwo further additions of GSGC (0.10 equiv) were added
  5. temperatureof reflux respectively
  6. temperatureThis was then cooled
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether
  9. customto yield a brown solid, 0.205 g, 12%

출처 및 근거

ORD 기록
ord-0f0e2fb597524808b586a83d932a8bd0
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710178B2

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