Diisopropylethylamine → tert-Butyl 3-((3-bromobenzyloxy)carbonylamino)propanoate

HRID 2175230ノート

反応式

HRID 2175230 の反応式
[C:1](=[O:21])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[CH:5]=1.C(N(C(C)C)C(C)C)C.Cl.[NH2:32][CH2:33][CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>C(Cl)Cl>[Br:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[CH2:3][O:2][C:1]([NH:32][CH2:33][CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:21]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 867125803-Bromobenzyl 4-nitrophenyl carbonate

生成物 1

HCID 70982800tert-Butyl 3-((3-bromobenzyloxy)carbonylamino)propanoate収率 91.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-bromobenzyl 4-nitrophenyl carbonate (8 g, 21.58 mmol) in DCM (50 mL) was added N-ethyl-N-isopropylpropan-2-amine (7.47 mL, 43.2 mmol) and tert-butyl 3-aminopropanoate hydrochloride (3.92 g, 21.58 mmol). Upon the completion of addition, the reaction mixture was stirred at room temperature for 1 h and then quenched with water. The resulting mixture was extracted with CH2Cl2 and the combined organic layer was dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-50% ethyl acetate:hexanes) to afford the title compound (7.10 g, 89% yield) as a light brown oil. LCMS, [M-tBu+2H]+=302.1. 1H NMR (400 MHz, CDCl3) δ 7.50 (s, 1H), 7.44 (d, J=7.7 Hz, 1H), 7.29-7.19 (m, 2H), 5.31 (br. s, 1H), 5.06 (s, 2H), 3.43 (dd, J=12.1, 6.1 Hz, 2H), 2.46 (t, J=6.0 Hz, 2H), 1.45 (s, 9H).

後処理

  1. additionUpon the completion of addition
  2. customquenched with water
  3. extractionThe resulting mixture was extracted with CH2Cl2
  4. dry with materialthe combined organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (0-50% ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-106df750ef9540c09fc5760194567fea
出典データセット
uspto-grants-2015_06
特許番号
US09062028B2

反応ノート

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