Triethylamine → (S)-2-tert-Butoxycarbonylamino-3-[4-(pyridin-4-yloxy)-phenyl]-propionic acid methyl ester

HRID 2369171노트

반응식

HRID 2369171 반응식
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[N:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:25]2[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=2)=[CH:8][CH:7]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 2734379(Pyridin-4-yl)boronic acidHCID 7019130Boc-Tyr-OMe

생성물 1

HCID 66922737(S)-2-tert-Butoxycarbonylamino-3-[4-(pyridin-4-yloxy)-phenyl]-propionic acid methyl ester수율 20.7%

시약·촉매·용매 3

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid methyl ester (8.46 mmol), 4-pyridyl boronic acid (29.6 mmol), Cu(OAc)2 (16.9 mmol), and molecular sieves were suspended in 25 mL of DCM. Triethylamine (59.2 mmol) was added and the mixture stirred at rt for 10 h. The mixture was diluted with ethyl acetate and washed with 10% sodium carbonate (6×). The organic layer was dried and concentrated under reduced pressure. The residue was purified over silica gel (hexanes-EtOAc) to provide (S)-2-tert-Butoxycarbonylamino-3-[4-(pyridin-4-yloxy)-phenyl]-propionic acid methyl ester (653 mg). LC-MS (m/z) 374.

후처리

  1. washwashed with 10% sodium carbonate (6×)
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified over silica gel (hexanes-EtOAc)

출처 및 근거

ORD 기록
ord-e4213c380a294ca6a91420ba9018a159
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703766B2

반응 노트

불러오는 중…