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

HRID 1684814ノート

反応式

HRID 1684814 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 was washed successively with 1N 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 was washed successively with 1N 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-35d18a1a962e4b69bdc1de88b9381d92
出典データセット
uspto-grants-2012_04
特許番号
USRE043298E1

反応ノート

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