Toluene → Benzyloxycarbonyl-L-proline

HRID 21765

反応式

HRID 21765 の反応式
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Cl[C:10]([O:12]C1C=CC=CC=1)=[O:11].[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[OH-].[Na+]>[C:10]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])([O:12][CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:11]

参加物

5

反応物 3

HCID 1140TolueneHCID 15891Phenyl chloroformateHCID 145742L-Proline

生成物 1

HCID 101987Benzyloxycarbonyl-L-proline収率 98%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒2 回

反応条件

温度
0 °C

実験手順

L-Proline (10 g, 86.6 mmol) was dissolved in 66 mL of 2N NaOH and cooled to 0° C. To this solution were slowly and simultaneously added 34.35 mL of a solution of phenyl chloroformate in toluene (104.2 mmol) and 33 mL of 4N NaOH, over a period of 1 hr, while maintaining the reaction temperature at 0° C. and the pH above 7. After all reactants were added, the reaction was stirred for 6 hr at room temperature. The solution was then extracted with ether. The remaining aqueous layer was neutralized to pH 6-7 with 1N HCl, then extracted with ethyl acetate. The extract was dried over Na2SO4 and concentrated to afford 21.19 g of the title product (98% yield). 1H NMR (CDCl3) δ 9.55 (d, 1H), 7.3 (s, 5H), 5.25 (d, 2H), 4.35 (t, 1H), 4.20 (t, 1H), 1.8-2.2 (m, 4H).

後処理

  1. temperaturewhile maintaining the reaction temperature at 0° C.
  2. additionAfter all reactants were added
  3. extractionThe solution was then extracted with ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c176d87d6c3c4a96ab95c902ab9d98fb
出典データセット
uspto-grants-1995_06
特許番号
US05424444

関連ノート

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