1,2-Dichloroethane → HCID 57733287、化合物

HRID 1920752ノート

反応式

HRID 1920752 の反応式
[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]([OH:14])=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:1]([N:5]1[CH2:6][CH2:7][CH:8]([CH2:11][C:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[CH2:9][CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 19439052HCID 19439052、化合物

生成物 1

HCID 57733287HCID 57733287、化合物収率 27%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of (1-tert-butyl-piperidin-4-yl)-acetic acid (672 mg, 3.37 mmol), aniline (0.32 ml, 3.5 mmol), and HOBt (568 mg, 4.2 mmol) in DMF (20 ml), EDC (805 mg, 4.2 mmol) was added. It was stirred at r.t. for 2 hours and partitioned between water (200 ml) and ethyl acetate (200 ml). The organic phase was washed with 0.5 N aq. NaOH (2×50 ml) and brine (3×50 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on (SiO2, gradient heptane-ethyl acetate) to give 250 mg of the title compound. 1H NMR (500 MHz, DMSO-d6): 1.07 (s, 9H), 1.32 (br. m, 2H), 1.81 (br. d, 2H), 1.89 (m, 1H), 2.11 (br. t, 2H), 2.25 (d, 2H), 3.03 (br. d, 2H), 7.1 (t, 1H), 7.24 (br., 1H), 7.31 (t, 2H), 7.52 (d, 2H).

後処理

  1. additionwas added
  2. custompartitioned between water (200 ml) and ethyl acetate (200 ml)
  3. washThe organic phase was washed with 0.5 N aq. NaOH (2×50 ml) and brine (3×50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on (SiO2, gradient heptane-ethyl acetate)

出典と根拠

ORDレコード
ord-c410419490784cfeb0be7049ed5e9ec5
出典データセット
uspto-grants-2012_05
特許番号
US08173639B2

反応ノート

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