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(+)-L-Leucine methyl ester → HCID 131731090, 화합물

HRID 1912376
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HRID 1912376 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 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

생성물 1

HCID 131731090HCID 131731090, 화합물
수율 70.3%

시약·촉매·용매 3

HCID 180Acetone용매2회HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-e5a406ac9df748afa2a896e1c3d1d731
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08609610B2

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