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(+)-L-Leucine methyl ester → HCID 131731090、化合物

HRID 1912376
ノート
印刷プレビュー

反応式

HRID 1912376 の反応式
[NH:1]([C:21]([O:23][CH2:24][CH:25]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[C@H:2]([C:18]([OH:20])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][CH:5]=1.[NH2:38][C@H:39]([C:44]([O:46][CH3:47])=[O:45])[CH2:40][CH:41]([CH3:43])[CH3:42].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.Cl.CC(C)=O>[NH:1]([C:21]([O:23][CH2:24][CH:25]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[C@H:2]([C:18]([NH:38][C@H:39]([C:44]([O:46][CH3:47])=[O:45])[CH2:40][CH:41]([CH3:43])[CH3:42])=[O:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])=[CH:6][CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 65105(+)-L-Leucine methyl esterHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27561174-((tert-Butoxycarbonyl)amino)-N-(((9H-fluoren-9-yl)methoxy)(hydroxy)methylidene)phenylalanine

生成物 1

HCID 131731090HCID 131731090、化合物
収率 70.3%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒2 回HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

Fmoc-Phe(4-NHBoc)-OH (210 mg, 418 μmol, 1 equiv.) was dissolved in DCM and HCl.H-Leu-OMe (77 mg, 460 μmol, 1.1 equiv.), HBTU (190 mg, 502 μmol, 1.2 equiv.) and DiPEA (242 μl, 1.46 mmol, 3.5 equiv.) were added and the mixture stirred for 1 hour. after which it was washed with 1M HCl (2×), sat. aq. NaHCO3 (4×) and brine and dried over MgSO4. Column chromatography (10% acetone:PE->20% acetone:PE) yielded the title compound (206 mg, 294 μmol, 70%). 1H NMR (400 MHz, CDCl3): δ ppm 7.76 (d, J=7.5 Hz, 2H), 7.54 (t, J=6.9 Hz, 2H), 7.39 (t, J=7.4 Hz, 2H), 7.35-7.20 (m, 4H), 7.11 (d, J=7.1 Hz, 2H), 6.54 (s, 1H), 6.29 (d, J=6.6 Hz, 1H), 5.44 (d, J=7.2 Hz, 1H), 4.55 (td, J=8.4, 5.4 Hz, 1H), 4.41 (dd, J=10.3, 7.2 Hz, 1H), 4.32 (s, 1H), 4.18 (t, J=6.9 Hz, 1H), 3.68 (s, 3H), 3.15-2.94 (m, 2H), 1.65-1.39 (m, 3H), 1.51 (s, 9H), 0.97-0.78 (m, 6H). 13C NMR (101 MHz, CDCl3): δ ppm 172.74, 170.69, 155.89, 152.64, 143.67, 143.60, 141.16, 137.31, 130.58, 129.83, 127.64, 127.01, 124.98, 119.88, 118.55, 80.41, 67.11, 55.88, 52.17, 50.75, 46.95, 41.31, 37.78, 28.25, 24.63, 22.58, 21.81.

後処理

  1. washafter which it was washed with 1M HCl (2×), sat. aq. NaHCO3 (4×) and brine
  2. dry with materialdried over MgSO4

出典と根拠

ORDレコード
ord-e5a406ac9df748afa2a896e1c3d1d731
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08609610B2

反応ノート

読み込み中…

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