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

HRID 52691

反応式

HRID 52691 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bfffcc8afd094599a091314af6b5ea06
出典データセット
uspto-grants-1997_04
特許番号
US05616720

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