Hydrochloric Acid → (Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester

HRID 1058427노트

반응식

HRID 1058427 반응식
CN(C)C(N(C)C)=N.[CH3:9][O:10][C:11](=[O:40])[CH:12](P(OC)(OC)=O)[NH:13][C:14](=[O:33])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)=[O:22])=[CH:17][C:16]=1Cl.[Br:41][C:42]1[CH:49]=[CH:48][C:45]([CH:46]=O)=[CH:44][CH:43]=1.[ClH:50]>O1CCCC1.O1CCOCC1>[CH3:9][O:10][C:11](=[O:40])/[C:12](/[NH:13][C:14](=[O:33])[C:15]1[CH:16]=[CH:17][C:18]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)=[O:22])=[CH:19][C:20]=1[Cl:50])=[CH:46]/[C:45]1[CH:48]=[CH:49][C:42]([Br:41])=[CH:43][CH:44]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 664601,1,3,3-TetramethylguanidineHCID 707414-BromobenzaldehydeHCID 23560750HCID 23560750, 화합물

생성물 1

HCID 59038409(Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester수율 62%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 312751,4-Dioxane용매

실험 절차

1,1,3,3-Tetramethylguanidine (0.047 g, 0.41 mmol) was added to a solution of rac.-N-[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (Example 141; 0.10 g, 0.21 mmol) and 4-bromobenzaldehyde (0.076 g, 0.412 mmol) in tetrahydrofuran (1.5 mL). Dioxane (1.5 mL) was added to bring everything into solution and the reaction mixture was stirred at room temperature for 15 h. The solution was then poured into 1N hydrochloric acid solution and the aqueous phase was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residual material was chromatographed over silica gel (45% ethyl acetate/hexanes) to give (Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester (69 mg, 62% yield).

후처리

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated in vacuo
  3. customthe residual material was chromatographed over silica gel (45% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-8fa00c8d5dd44fd08da5f7d45474c37c
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515124B2

반응 노트

불러오는 중…