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Diisopropylethylamine → HCID 86655579, 화합물

HRID 39280
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HRID 39280 반응식
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([P:12]([O:23][CH2:24][CH3:25])([CH2:14][P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])=[O:13])=[CH:8][C:7]=1[C:26]([CH3:32])([CH3:31])[CH2:27][C:28](O)=[O:29])(=[O:4])[CH2:2][CH3:3].[CH3:33]CN(C(C)C)C(C)C.CN(C(ON1N=N[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][C:51]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.C([O:74][C:75](=[O:85])[C@H:76]([CH2:78][C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1)[NH2:77])C1C=CC=CC=1>CN(C=O)C.C(OCC)(=O)C>[CH2:33]([N:77]([C:28](=[O:29])[CH2:27][C:26]([C:7]1[CH:8]=[C:9]([P:12]([O:23][CH2:24][CH3:25])([CH2:14][P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])=[O:13])[CH:10]=[CH:11][C:6]=1[O:5][C:1](=[O:4])[CH2:2][CH3:3])([CH3:31])[CH3:32])[C@H:76]([C:75]([OH:74])=[O:85])[CH2:78][C:79]1[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12636208Benzyl L-phenylalaninate hydrochloride (1:1)HCID 86655578HCID 86655578, 화합물

생성물 1

HCID 86655579HCID 86655579, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of acid 124 (319 mg, 0.648 mmol) in DMF (5 mL) at 0° C. was added DIEA (226 μL, 130 mmol) and HBTU (246 mg, 0.648 mmol). After stirring for 15 min at 0° C., L-Phenylalanine benzyl ester hydrochloride (189 mg, 0.648 mmol) was added and stirring was continued while warming to room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with H2O and saturated aqueous NaCl then dried over Na2SO4. The crude product was purified by silica gel chromatography (gradient of 0 to 20% methanol in ethyl acetate) using a Biotage Horizons™ system. Compound 125 was obtained as a colourless liquid (150 mg, 32%). 1H NMR (400 MHz, CDCl3) δ 1.20 (t, J=7.0, 3H), 1.21 (t, J=7.0, 3H), 1.25-1.32 (m, 18H), 1.44 (s, 3H), 1.45 (s, 3H), 1.47 (s, 3H), 1.48 (s, 3H), 2.47-2.67 (m, 12H), 2.87 (bd, J=6.2, 4H), 3.89-4.18 (m, 12H), 5.03 (AB q, J=12.3, 2H), 5.05 (AB q, J=12.3, 2H), 5.88 (bt, J=8.8, 2H), 6.91-6.95 (m, 4H), 7.01 (ddd, J=3.5, 5.2, 8.7, 2H), 7.17-7.23 (m, 10H), 7.31-7.32 (m, 6H), 7.71 (ddd, J=1.8, 8.1, 11.6, 1H), 7.75 (ddd, J=1.8, 8.1, 11.6, 1H), 7.86 (t, J=14.0, 1H), 7.87 (t, J=14.0, 1H): 31P (162 MHz, CDCl3) δ 20.31 (d, J=4.9, 1 P), 20.37 (d, J=4.9, 1 P), 33.93 (bd, J=9.5, 2P).

후처리

  1. stirringstirring
  2. temperaturewhile warming to room temperature overnight
  3. washwashed with H2O and saturated aqueous NaCl
  4. dry with materialthen dried over Na2SO4
  5. customThe crude product was purified by silica gel chromatography (gradient of 0 to 20% methanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-1803c4a5359a46dc9153a2507a5f8659
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08524691B2

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