홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Hydrochloric Acid → (S)-4-methyl-2-[4-(naphthalen-1-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-pentanoic acid

HRID 19075
노트
인쇄 미리보기

반응식

HRID 19075 반응식
C[O:2][C:3](=[O:26])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]1=[O:25])[CH2:5][CH:6]([CH3:8])[CH3:7].O.[OH-].[Li+].Cl>O1CCCC1.O>[CH3:7][CH:6]([CH3:8])[CH2:5][C@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]1=[O:25])[C:3]([OH:26])=[O:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66894649(S)-4-methyl-2-[4-(naphthalen-1-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-pentanoic acid methyl ester

생성물 1

HCID 66894352(S)-4-methyl-2-[4-(naphthalen-1-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-pentanoic acid수율 100.9%

시약·촉매·용매 2

HCID 962Water
용매
2회
HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

A mixture of (S)-4-methyl-2-[4-(naphthalen-1-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-pentanoic acid methyl ester (0.38 g, 1.08 mmol) in tetrahydrofuran (8.1 mL) and water (2.7 mL) was treated with lithium hydroxide monohydrate (54 mg, 1.3 mmol). The reaction was stirred at 25° C. for 2 h. At this time, the reaction was diluted with water (50 mL), acidified with a 2N aqueous hydrochloric acid solution and then extracted with 10% methanol/dichloromethane (3×50 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford (S)-4-methyl-2-[4-(naphthalen-1-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-pentanoic acid (0.37 g, 99%) as a pale yellow solid: HR-ES-MS m/z calculated for C20H21NO4 [M+H]+ 340.1544, observed 340.1545; The material was used without further purification. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.88 (d, J=6.3 Hz, 3H), 0.95 (d, J=6.3 Hz, 3H), 1.43-1.88 (m, 3H), 4.33 (d, J=18.1 Hz, 1H), 4.42 (d, J=18.1 Hz, 1H), 4.64 (dd, J=11.3, 4.4 Hz, 1H), 4.74 (s, 1H), 7.51 (d, J=7.5 Hz, 1H), 7.54-7.68 (m, 3H), 7.91 (d, J=8.2 Hz, 1H), 7.96-8.09 (m, 2H), 12.89 (br. s., 1H).

후처리

  1. extractionextracted with 10% methanol/dichloromethane (3×50 mL)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ff20aad6d48649bd8ceb7e79336e45e4
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07741327B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트