Dimethylformamide → (R)-3-[4-(4-Benzoyl-phenoxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid methyl ester

HRID 1669498ノート

反応式

HRID 1669498 の反応式
CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:12][O:13][C:14](=[O:32])[C@@H:15]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].F[C:34]1[CH:47]=[CH:46][C:37]([C:38]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:39])=[CH:36][CH:35]=1>O>[CH3:12][O:13][C:14](=[O:32])[C@H:15]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:43]2[CH:44]=[CH:45][C:40]([C:38](=[O:39])[C:37]3[CH:46]=[CH:47][CH:34]=[CH:35][CH:36]=3)=[CH:41][CH:42]=2)=[CH:27][CH:26]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 676634-FluorobenzophenoneHCID 7016055Boc-D-Tyr-OMe

生成物 1

HCID 67351929(R)-3-[4-(4-Benzoyl-phenoxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid methyl ester収率 24%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of N,N-Dimethylformamide (DMF) (3.16 mL) and potassium carbonate (0.222 g, 1.605 mmol) was added Boc-D-Tyrosine-Methyl ester (0.158 g, 0.535 mmol) and 4-Fluorobenzophenone (0.160 g, 0.802 mmol) at 100° C. under an atmosphere of nitrogen for 42 hours. The mixture was poured into 30 mL water solution and extracted with ethyl acetate (EtOAc) (4×10 mL). The combined organic layers were washed with brine (40 mL) and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo to obtain the crude mixture, which was purified by of silica gel flash chromatography, using EtOAc/hexane (gradient system), to obtain the product (0.060 g, 24%): 1H NMR (400 MHz, CDCL3): δ 1.42 (s, 9H), 2.99-3.17 (m, 2H), 3.71-3.74 (m, 3H), 4.53-4.61 (m, 1H), 4.96-5.16 (m, 1H), 6.75 (d, 1H, J=8.4 Hz), 6.97-7.03 (m, 4H), 7.16 (d, 2H, J=8.4 Hz), 7.46-7.50 (m, 2H), 7.56-7.58 (m, 1H), 7.77-7.83 (m, 3H).

後処理

  1. extractionextracted with ethyl acetate (EtOAc) (4×10 mL)
  2. washThe combined organic layers were washed with brine (40 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationThe organic layer was concentrated in vacuo
  5. customto obtain the crude mixture, which
  6. customwas purified by of silica gel flash chromatography

出典と根拠

ORDレコード
ord-4f9f6772dec54df5a2f6747c8b71c3a7
出典データセット
uspto-grants-2011_08
特許番号
US07989480B2

反応ノート

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