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Diisopropylethylamine → HCID 86655579、化合物

HRID 39280
ノート
印刷プレビュー

反応式

HRID 39280 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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、化合物

生成物 1

HCID 86655579HCID 86655579、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1803c4a5359a46dc9153a2507a5f8659
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08524691B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート