Triethylamine → HCID 178501494, 화합물

HRID 17113

반응식

HRID 17113 반응식
S([O-])([O-])(=O)=O.[Mg+2].[Br:7][C:8]1[N:13]=[C:12]([CH:14]=O)[CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.Cl.[CH3:24][O:25][C:26](=[O:32])[C@H:27]([CH:29]([CH3:31])[CH3:30])[NH2:28]>>[CH3:24][O:25][C:26](=[O:32])[C@@H:27](/[N:28]=[CH:14]/[C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:7])[N:13]=1)[CH:29]([CH3:31])[CH3:30]

참가 물질

5

반응물 4

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 111190Methyl valinate hydrochlorideHCID 27570096-Bromopyridine-2-carbaldehyde

생성물 1

HCID 178501494HCID 178501494, 화합물

실험 절차

Anhydrous magnesium sulfate (5.4 g), 6-bromopyridine-2-carboxaldehyde (5.0 g, 26.9 mmol) and triethylamine (3.75 mL, 26.9 mmol) were each added sequentially in one portion to a cooled (0° C.) solution of (L)-valine methyl ester hydrochloride (4.51 g, 26.9 mmol) and the reaction mixture was allowed to warm slowly to room temperature overnight under a nitrogen atmosphere. The mixture was then filtered and the filter cake washed with diethyl ether (100 mL) before evaporating the filtrate in vacuo. The residue was purified by column chromatography using 5:1 hexane/ethyl acetate as eluent to yield A469.1 (7.1 g, 88%). HPLC YMC S-5 4.6×33 mm (2 min grad): retention time 0.86 min, M+H+=202.08

후처리

  1. additioneach added sequentially in one portion to
  2. filtrationThe mixture was then filtered
  3. washthe filter cake washed with diethyl ether (100 mL)
  4. custombefore evaporating the filtrate in vacuo
  5. customThe residue was purified by column chromatography
  6. customto yield A469.1 (7.1 g, 88%)
  7. custom4.6×33 mm (2 min grad)

출처 및 근거

ORD 기록
ord-579292326f8242fabf3213cdbc438ee7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737279B2

연결된 노트

불러오는 중…