Hydrochloric Acid → HCID 86597662, 화합물

HRID 350754노트

반응식

HRID 350754 반응식
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]([P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])[OH:7])=[CH:4][CH:3]=1.[N:18]1([C:27]2[O:28][C:29]([CH2:39][CH2:40][C:41](O)=[O:42])=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[N:31]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[CH:19]1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O>[N:18]1([C:27]2[O:28][C:29]([CH2:39][CH2:40][C:41]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([CH:6]([P:8]([O:9][CH2:10][CH3:11])([O:12][CH2:13][CH3:14])=[O:15])[OH:7])=[CH:16][CH:17]=3)=[O:42])=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[N:31]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[CH:19]1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 21088585HCID 21088585, 화합물HCID 23061737Diethyl P-[(4-aminophenyl)hydroxymethyl]phosphonate

생성물 1

HCID 86597662HCID 86597662, 화합물수율 58.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of diethyl 4-amino-α-hydroxybenzylphosphonate (50 mg), 3-{3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]propionic acid (54 mg), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (38 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (43 mg) and N,N-dimethylformamide (0.5 ml) was stirred overnight at room temperature. To the reaction mixture was added 0.1N aqueous hydrochloric acid solution (2 ml) and the reaction mixture was extracted with ethyl acetate (2 ml). The organic layer was concentrated, introduced into preparative HPLC and purified to give 3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]-N-(4-[(diethylphosphono)(hydroxy)methyl]phenyl}propionamide (52 mg, 58%). Recrystallization from ethyl acetate-isopropyl ether gave yellow prism crystals. melting point: 171–172° C. MS (ESI+): 609 (M+H)

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate (2 ml)
  2. concentrationThe organic layer was concentrated
  3. additionintroduced into preparative HPLC
  4. custompurified

출처 및 근거

ORD 기록
ord-7b4ec0dce8374ff9a23c02e94f45fe50
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183276B2

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