Diisopropylethylamine → HCID 54402107、化合物

HRID 1912370ノート

反応式

HRID 1912370 の反応式
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN([C:23]([O:27][N:28]1N=NC2C=CC(=C[C:29]1=2)Cl)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:23][O:27][N:28]([CH3:29])[C:17](=[O:19])[C@@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:10][C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 7020844(2S)-2-(((tert-butoxy)carbonyl)amino)-3-(pyridin-4-yl)propanoic acidHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate

生成物 1

HCID 54402107HCID 54402107、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of Boc-β-(4-pyridyl)-L-alanine (75, 300 mg, 1.08 mmol) and NH(Me) OMe.HCl (1.2 eq., 1.30 mmol, 129 mg) in DCM (10 mL) was added HCTU (1.2 eq., 1.30 mmol, 536 mg) and DiPEA (3.5 eq., 3.78 mmol, 625 μL) and the mixture was stirred for 1 hour after which TLC analysis indicated complete conversion of starting material. The solvent was evaporated under reduced pressure en the residue was taken up in EtOAc, extracted with sat. aq. NaHCO3 (2×) and brine, dried over MgSO4 and concentrated in vacuo. The title compound was obtained after purification by column chromatography (EtOAc->2% MeOH/EtOAc) as a pale yellow solid (yield: 334 mg, 1.08 mmol, quant.). 1H NMR (400 MHz, CD3OD): δ=8.40 (d, J=4.59 Hz, 2H), 7.29 (d, J=4.88 Hz, 2H), 6.97 (d, J=7.26 Hz, 1H), 4.77-4.68 (m, 1H), 3.76 (s, 3H), 3.15 (s, 3H), 3.02 (dd, J=13.59, 4.85 Hz, 1H), 2.83-2.77 (m, 1H), 1.32 (s, 9H) ppm. 13C NMR (100 MHz, CD3OD): δ=173.49, 157.58, 149.88, 149.50, 126.48, 80.55, 62.25, 52.71, 38.03, 32.49, 28.66 ppm. [α]D23=−2.9 (c=1, MeOH). HRMS: calcd. for C15H43N3O4 [M+H]+310.17613. found 310.17615.

後処理

  1. customThe solvent was evaporated under reduced pressure en the residue
  2. extractionextracted with sat. aq. NaHCO3 (2×) and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b246759d0d094b8a9ea3cec9be19278a
出典データセット
uspto-grants-2013_12
特許番号
US08609610B2

反応ノート

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