Water → 2-(Piperidin-1-yl)ethyl 3-(benzyloxycarbonylamino)-3-methylbutanoate

HRID 2061042

反応式

HRID 2061042 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:18])([CH3:17])[CH2:13][C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.O[CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.O>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:18])([CH3:17])[CH2:13][C:14]([O:16][CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 18232N-PiperidinoethanolHCID 682631,1'-CarbonyldiimidazoleHCID 145510073-(((Benzyloxy)carbonyl)amino)-3-methylbutanoic acid

生成物 1

HCID 601344582-(Piperidin-1-yl)ethyl 3-(benzyloxycarbonylamino)-3-methylbutanoate収率 71.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-(benzyloxycarbonylamino)-3-methylbutanoic acid (reported in international publication number WO 2008/083347 A1) (9.18 g, 36.5 mmol) in N,N-dimethylformamide (200 ml) was added N,N-carbonyldiimidazole (6.52 g, 40.2 mmol). The reaction mixture was stirred for 1 hour at room temperature followed by the addition of 1-(2-hydroxyethyl)piperidine (36.3 ml, 47.4 mmol) was added was added to the reaction mixture. The mixture was stirred for an additional 18 hours at room temperature. The reaction mixture was poured into water and was extracted with ethyl acetate. The organic layer was washed two more times with water and dried over sodium sulfate. The dried organic layer was filtered and concentrated in vacuo. The crude product was purified column chromatography (0 to 10% methanol in dichloromethane) to give 9.45 g (71% yield) of 2-(piperidin-1-yl)ethyl 3-(benzyloxycarbonylamino)-3-methylbutanoate. 1H NMR (CDCl3) δ 7.44-7.26 (m, 5 H), 5.47 (s, 1 H), 5.06 (s, 2 H), 4.19 (t, J=6.0 Hz, 2 H), 2.69 (s, 2 H), 2.50 (t, J=6.0 Hz, 2 H), 2.40-2.32 (m, 4 H), 1.60-1.48 (m, 4 H) 1.46-1.36 (m, 8 H); MS (ESI+) calculated for C20H31N2O4: 362.23, Found: 363.2 (M+H+).

後処理

  1. additionwas added
  2. additionwas added to the reaction mixture
  3. stirringThe mixture was stirred for an additional 18 hours at room temperature
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed two more times with water
  6. dry with materialdried over sodium sulfate
  7. filtrationThe dried organic layer was filtered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified column chromatography (0 to 10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-81a4ef065bd84c5484e690c364da3bc3
出典データセット
uspto-grants-2012_10
特許番号
US08278482B2

関連ノート

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