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Hydrochloric Acid → 2-{2-[5(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro [1,3,4]thiadiazol-2-yl]-phenoxymethyl}-furan-3-carboxylic acid

HRID 1046942
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HRID 1046942 반응식
C[O:2][C:3]([C:5]1[CH:9]=[CH:8][O:7][C:6]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[N:22]([C:23](=[O:33])[C:24]2[C:29]([F:30])=[CH:28][C:27]([F:31])=[CH:26][C:25]=2[F:32])[N:21]=[C:20]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[S:19]1)=[O:4].[Li+].[OH-].Cl>C1COCC1.CO.O>[F:40][C:37]1[CH:36]=[CH:35][C:34]([C:20]2[S:19][CH:18]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][CH2:10][C:6]3[O:7][CH:8]=[CH:9][C:5]=3[C:3]([OH:4])=[O:2])[N:22]([C:23](=[O:33])[C:24]3[C:29]([F:30])=[CH:28][C:27]([F:31])=[CH:26][C:25]=3[F:32])[N:21]=2)=[CH:39][CH:38]=1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 672793392-{2-[5(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-furan-3-carboxylic acid methyl ester

생성물 1

HCID 580256232-{2-[5(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro [1,3,4]thiadiazol-2-yl]-phenoxymethyl}-furan-3-carboxylic acid

시약·촉매·용매 1

HCID 21892291
Methanol tetrahydrofuran water
용매

실험 절차

To a solution of 2-{2-[5(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-furan-3-carboxylic acid methyl ester (0.49 mmol) in THF/MeOH/H2O (3:2:1), is added LiOH (3 N) (4.9 mmol). After stirring for 12 hours, the reaction is acidified with HCl (1 N) and extracted with ethyl acetate. The organic layer is dried over MgSO4, filtered, and concentrated. The residue is purified using preparative LC/MS to give 2-{2-[5(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-furan-3-carboxylic acid as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.26-7.23 (m, 3H), 7.20 (d, J=1.9, 1H), 7.10-7.05 (m, 1H), 7.03-6.99 (m, 1H), 6.86 (d, J=8.1, 1H), 6.78-6.74 (m, 3H), 6.55 (d, J=1.9, 1H), 6.55-6.50 (m, 2H), 5.38-5.21 (m, 2H); LC/MS (ES+): 557.1 (M+1)+.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified

출처 및 근거

ORD 기록
ord-b864df30adb24acbaab817d888c2365d
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569345B2

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