(R)-(-)-2-Amino-1-propanol → 5-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amide

HRID 600499노트

반응식

HRID 600499 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[N:16]=[CH:17][C:18]([C:21]([OH:23])=O)=[N:19][CH:20]=3)=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.[NH2:24][C@@H:25]([CH2:27][OH:28])[CH3:26].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.Cl.CN(C)CCCN=C=NCC>C1COCC1.O>[OH:28][CH2:27][C@@H:25]([NH:24][C:21]([C:18]1[CH:17]=[N:16][C:15]([O:14][CH2:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:9][O:10][CH:11]=2)=[CH:20][N:19]=1)=[O:23])[CH3:26]

참가 물질

8

반응물 5

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 684440725-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid

생성물 1

HCID 469379035-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amide수율 42%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-[3-(4-chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid (80 mg, 0.24 mmol) and D-alaninol (22.8 □L, 0.29 mmol) in THF (7 mL) was added 1-hydroxybenzotriazole hydrate (37.3 mg, 0.24 mmol), N-ethyldiisopropylamine (105.2 □L, 0.60 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (47.1 mg, 0.24 mmol) at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 72 h. Then the reaction mixture was diluted with water (10 mL), and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=1:1 to 2:3) afforded the title product (39 mg, 42%) which was obtained as white solid. MS: m/e=389.0 [M+H]+.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were then washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=1:1 to 2:3)

출처 및 근거

ORD 기록
ord-33d878a95fb647a485567de844601b1f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902201B2

반응 노트

불러오는 중…