Diisopropylethylamine → Fmoc-Phe-Gly-OH

HRID 39262

반응식

HRID 39262 반응식
[C:1]([NH:18][C@H:19]([C:27](O)=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O:67][C:68](=[O:71])[CH2:69][NH2:70])(C)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH:16]1[C:17]2[CH:5]([CH2:4][O:3][C:1]([NH:18][C@H:19]([C:27]([NH:70][CH2:69][C:68]([OH:67])=[O:71])=[O:28])[CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:2])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 151417Glycine tert-butyl esterHCID 978331Fmoc-phenylalanineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 11328236Fmoc-Phe-Gly-OH

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of Fmoc-phenylalanine (1.0 g, 2.58 mmol) in DMF (13 mL) at 0° C. was added DIEA (899 μL, 5.16 mmol) and HBTU (979 mg, 2.58 mmol). After stirring for 10 min at 0° C., glycine t-butyl ester (353 μL, 2.58 mmol) was added and stirring was pursued for 1 h at 0° C. The reaction mixture was diluted with ethyl acetate, washed with H2O, 1N HCl solution, saturated NaHCO3 solution and saturated NaCl solution. The organic layer was dried over MgSO4, filtered and concentrated to dryness. The crude product was purified by silica gel chromatography on a Biotage™ flash chromatography system using 50% ethyl acetate in hexanes. Dipeptide 72 was obtained as a white solid (1.05 g, 81%). 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 3.08-3.13 (m, 2H), 3.78-3.95 (m, 2H), 4.18 (t, J=6.9 Hz, 1H), 4.31-4.37 (m, 2H), 4.40-4.47 (m, 1H), 5.27 (bs, 1H), 6.21 (bs, 1H), 7.17-7.22 (m, 2H), 7.24-7.32 (m, 5H), 7.40 (t, J=7.5 Hz, 2H), 7.53 (t, J=7.9 Hz, 2H), 7.76 (d, J=7.5 Hz, 2H).

후처리

  1. stirringstirring
  2. waitwas pursued for 1 h at 0° C
  3. washwashed with H2O, 1N HCl solution, saturated NaHCO3 solution and saturated NaCl solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified by silica gel chromatography on a Biotage™ flash chromatography system

출처 및 근거

ORD 기록
ord-3a2396e3979d41b789dae883487b5654
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524691B2

연결된 노트

불러오는 중…