1,2-Dichloroethane → tert-butyl N-((2S)-1-oxopentan-2-yl)carbamate

HRID 734204ノート

反応式

HRID 734204 の反応式
[C:1]([NH:8][C@H:9]([CH2:13][OH:14])[CH2:10][CH2:11][CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1(C)C=CC=CC=1.C(Cl)CCl.ClC(Cl)C(O)=O>CS(C)=O>[C:1]([NH:8][C@H:9]([CH:13]=[O:14])[CH2:10][CH2:11][CH3:12])([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 1140TolueneHCID 6597Dichloroacetic AcidHCID 13969854(S)-tert-Butyl (1-hydroxypentan-2-yl)carbamate

生成物 1

HCID 10262225tert-butyl N-((2S)-1-oxopentan-2-yl)carbamate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
0 °C

実験手順

To Boc-norvalinol (7.77 g, 38 mmol), in anhydrous dimethylsulfoxide (153 mL) and toluene (153 mL) was added EDC (73.32 g, 382 mmol). After the solution was cooled to 0° C., dichloroacetic acid (15.8 mL, 191 mmol) was added dropwise. After addition was complete, the reaction was stirred for 15 min. The solution was allowed to warm to room temperature over a period of 2 h. The reaction mixture was concentrated to remove the toluene, then dissolved in ethyl acetate. The solution washed successively with 1 N sodium bisulfate, saturated sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated to afford crude Boc-norvalinal which was used directly in the next step. TLC Rf=0.84 (40% ethyl acetate/hexanes).

後処理

  1. additionAfter addition
  2. temperatureto warm to room temperature over a period of 2 h
  3. concentrationThe reaction mixture was concentrated
  4. customto remove the toluene
  5. dissolutiondissolved in ethyl acetate
  6. washThe solution washed successively with 1 N sodium bisulfate, saturated sodium bicarbonate and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-0a2beae3e1df40098ad56f2c0215fede
出典データセット
uspto-grants-2009_09
特許番号
US07592316B2

反応ノート

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