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Trifluoroacetic acid → HCID 68732367、化合物

HRID 1685767
ノート
印刷プレビュー

反応式

HRID 1685767 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 2

HCID 68732367HCID 68732367、化合物収率 100.6%HCID 86646456HCID 86646456、化合物

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

[(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.

後処理

  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

出典と根拠

ORDレコード
ord-e9adf66d9d4b4b4f9d238ac45e9f4dc5
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08148410B2

反応ノート

読み込み中…

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