4-Methylmorpholine → Methyl N-[(4-nitrophenoxy)carbonyl]-L-valinate

HRID 52691

반응식

HRID 52691 반응식
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].Cl.[CH3:15][O:16][C:17](=[O:23])[C@H:18]([CH:20]([CH3:22])[CH3:21])[NH2:19].CN1CCOCC1>C(Cl)Cl>[CH3:15][O:16][C:17](=[O:23])[C@H:18]([CH:20]([CH3:22])[CH3:21])[NH:19][C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3]

참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 111190Methyl valinate hydrochloride

생성물 1

HCID 15344176Methyl N-[(4-nitrophenoxy)carbonyl]-L-valinate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 66.1 g (0.328 mol) of 4-nitrophenyl chloroformate in 1.2 liters of CH2Cl2 was cooled to 0° C. and treated with L-valine methyl ester hydrochloride. The resulting mixture was treated slowly, with stirring, with 68.9 ml (0.626 mol) of 4-methylmorpholine. The resulting solution was allowed to slowly warm to ambient temperature and was stirred overnight. After washing with 3 portions of 10% aqueous NaHCO3, the solution was dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography by eluting with chloroform to provide the desired compound. 1H NMR (DMSO-d6) δ0.94 (d, J=7 Hz, 3H), 0.95 (d, J=7 Hz, 3H), 2.12 (octet, J=7 Hz, 1H), 3.69 (s, 3H), 4.01 (dd, J=8, 6 Hz, 1H), 7.41 (dt, J=9, 3 Hz, 2H), 8.27 (dt, J=9, 3 Hz, 2H), 8.53 (d, J=8 Hz, 1H). Mass spectrum: (M+NH4)+ =314.

후처리

  1. additionThe resulting mixture was treated slowly
  2. washAfter washing with 3 portions of 10% aqueous NaHCO3
  3. dry with materialthe solution was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washby eluting with chloroform

출처 및 근거

ORD 기록
ord-bfffcc8afd094599a091314af6b5ea06
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616720

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