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Trifluoroacetic acid → HCID 68732367, 화합물

HRID 1685767
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HRID 1685767 반응식
[CH2:1]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][NH2:25])=[CH:19][CH:18]=3)[N:13]=2)=[CH:9][C:8]=1[CH3:26])[CH2:4][CH3:5])[CH3:2].[C:27]([O:31][C:32]([N:34]([CH2:36][C:37]([OH:39])=[O:38])[CH3:35])=[O:33])([CH3:30])([CH3:29])[CH3:28].C(O)(C(F)(F)F)=O>C(Cl)Cl.CC(=O)OCC>[C:27]([O:31][C:32](=[O:33])[N:34]([CH2:36][C:37](=[O:38])[NH:25][CH2:24][CH2:23][C:20]1[CH:19]=[CH:18][C:17]([C:14]2[N:13]=[C:12]([C:10]3[S:11][C:7]([CH2:6][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[C:8]([CH3:26])[CH:9]=3)[O:16][N:15]=2)=[CH:22][CH:21]=1)[CH3:35])([CH3:30])([CH3:28])[CH3:29].[CH2:1]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][NH:25][C:37](=[O:39])[CH2:36][NH:34][CH3:35])=[CH:21][CH:22]=3)[N:13]=2)=[CH:9][C:8]=1[CH3:26])[CH2:4][CH3:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 6422Trifluoroacetic acidHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 67265437HCID 67265437, 화합물

생성물 2

HCID 68732367HCID 68732367, 화합물수율 100.6%HCID 86646456HCID 86646456, 화합물

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 8857Ethyl Acetate용매

실험 절차

[(2-{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethylcarbamoyl)-methyl]-methyl-carbamic acid tert-butyl ester is prepared in analogy to Example 163 by coupling 2-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethylamine (20 mg, 54 μmol) with (tert-butoxycarbonyl-methyl-amino)-acetic acid (15 mg, 81 μmol); LC-MS: tR=0.84 min; [M+1]+=542.20; 1H NMR (CDCl3): δ1.16 (m, 6H), 1.44 (s, 9H), 2.27 (s, 3H), 2.88 (s, 3H), 2.90-2.99 (m, 2H), 3.61 (q, J=6.5 Hz, 2H), 3.75 (s br, 1H), 3.85 (s, 2H), 7.34 (d, J=8.0 Hz, 2H), 7.67 (s, 1H), 8.10 (d, J=8.0 Hz, 2H). This material (18 mg, 30 μmol) is dissolved in DCM (2 mL) and TFA (50 μL) is added. The mixture is stirred at rt for 18 h before it is diluted with EA and washed with sat. aq. NaHCO3 solution. The organic extract is dried over Na2SO4, filtered and concentrated. The crude product is purified by prep. HPLC and on prep. TLC plates with DCM containing 10% of 7 N NH3 in methanol to give the title compound (12 mg) as a colourless solid; LC-MS: tR=0.64 min; [M+1]+=442.00.

후처리

  1. washwashed with sat. aq. NaHCO3 solution
  2. extractionThe organic extract
  3. dry with materialis dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by prep

출처 및 근거

ORD 기록
ord-e9adf66d9d4b4b4f9d238ac45e9f4dc5
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08148410B2

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