Hexane → tert-Butyl pentanoate

HRID 1603237

反応式

HRID 1603237 の反応式
[CH3:1][C:2]([O:5][C:6](=[O:15])[CH:7](CCC)[CH2:8][CH2:9][CH2:10]N)([CH3:4])[CH3:3].C1C([N+]([O-])=O)=CC=C([Cl-]C([O-])=O)C=1.C(=O)(O)[O-].[Na+].CCCCCC>O.ClCCl>[CH3:4][C:2]([O:5][C:6](=[O:15])[CH2:7][CH2:8][CH2:9][CH3:10])([CH3:1])[CH3:3]

参加物

6

反応物 3

HCID 8058HexaneHCID 516892Sodium BicarbonateHCID 54566902Rac-5-amino-2-propylpentanoic acid 1,1-dimethylethyl ester

生成物 1

HCID 520048tert-Butyl pentanoate

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 160 mg (0.74 mmol) of rac-5-amino-2-propylpentanoic acid 1,1-dimethylethyl ester (8) in 1 mL of water and 1 mL of dichloromethane, 153 mg (0.76 mmol) of 4-nitrophenylchloroformate and 267 mg of sodium bicarbonate were added at 0° C. The mixture was stirred at room temperature overnight and then diluted with 50 mL of dichloromethane and 30 mL of water. The organic part was separated. The aqueous part was extracted with 2×50 mL of dichloromethane. The organic parts were combined and washed with 2×50 mL of 5% sodium bicarbonate followed by 50 mL of water, dried over MgSO4 and concentrated. The residue was purified by preparative thin layer chromatography using 1:1 ethyl acetate:hexane as the eluent to yield 185 mg (0.48 mmol, 66%) of rac-5-[[(4-nitrophenoxy)carbonyl]amino]-2-propyl]pentanoic acid 1,1-dimethylethyl ester (9) asan offwhite solid. NMR, IR and MS data confirmed compound identity.

後処理

  1. additionwere added at 0° C
  2. customThe organic part was separated
  3. extractionThe aqueous part was extracted with 2×50 mL of dichloromethane
  4. washwashed with 2×50 mL of 5% sodium bicarbonate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-45272e5fe07644308eb9327e9331cecf
出典データセット
uspto-grants-1999_11
特許番号
US05986094

関連ノート

読み込み中…