Dimethyl Sulfoxide → N-p-toluoyl valinaldehyde

HRID 1835252노트

반응식

HRID 1835252 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([CH3:26])[CH:16]=[CH:15][C:14]([C:17]([NH:19][C@H:20]([CH2:24][OH:25])[CH:21]([CH3:23])[CH3:22])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[C:11]1([CH3:26])[CH:12]=[CH:13][C:14]([C:17]([NH:19][C@H:20]([CH:24]=[O:25])[CH:21]([CH3:23])[CH3:22])=[O:18])=[CH:15][CH:16]=1

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18346087N-p-toluoyl valinol

생성물 1

HCID 53763109N-p-toluoyl valinaldehyde수율 56.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

Dimethylsulfoxide (2.2 ml, 31 mmol ) was slowly added via syringe to a stirred −78° C. solution of oxalyl chloride (15 ml, 171 mmol) in methylene chloride (35 ml) under inert. atmosphere. After 10 min., a solution of N-p-toluoyl valinol (6.0 g, 29 mmol) in methylene chloride (50 ml) was added and the stirring was continued for additional 15 min. Triethylamine was added (6 ml, 389 mmol) and the reaction was allowed to warm to ambient temperature. After 1.5 h, the reaction was diluted with 50% ethyl acetate in hexanes and washed with water and brine. Filtration through a pad of silica gel and subsequent solvent removal left a solid residue. Chromatography eluting with 20% ethyl acetate in hexanes, then 33% ethyl acetate in hexanes gave N-p-toluoyl valinaldehyde (3.6 g) as a solid, which was utilized in Step 6.

후처리

  1. waitthe stirring was continued for additional 15 min
  2. waitAfter 1.5 h
  3. washwashed with water and brine
  4. filtrationFiltration
  5. customthrough a pad of silica gel and subsequent solvent removal
  6. waitleft a solid residue
  7. washChromatography eluting with 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-221717eb54fb4f3586150e8d5903674c
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06770650B2

반응 노트

불러오는 중…