Hexane → tert-Butyl pentanoate

HRID 1603237

반응식

HRID 1603237 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 520048tert-Butyl pentanoate

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-45272e5fe07644308eb9327e9331cecf
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05986094

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