Phosgene → tert-Butyl N-allyl-N-{[allyl(cyclopropylmethyl)amino]carbonyl}glycinate

HRID 1442869ノート

反応式

HRID 1442869 の反応式
[CH2:1]([NH:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH:2]=[CH2:3].[C:13](Cl)(Cl)=[O:14].C(N(CC)CC)C.[CH:24]1([CH2:27][NH:28][CH2:29][CH:30]=[CH2:31])[CH2:26][CH2:25]1>C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([N:4]([C:13]([N:28]([CH2:29][CH:30]=[CH2:31])[CH2:27][CH:24]1[CH2:26][CH2:25]1)=[O:14])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH:2]=[CH2:3]

参加物

7

反応物 4

HCID 6371PhosgeneHCID 8471Triethylamine2 回HCID 19959470Tert-butyl 2-[(prop-2-en-1-yl)amino]acetateHCID 20460830N-2-Propen-1-ylcyclopropanemethanamine

生成物 1

HCID 18442657tert-Butyl N-allyl-N-{[allyl(cyclopropylmethyl)amino]carbonyl}glycinate

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To an ice-cooled solution of tert-butyl N-allylglycinate (Senokuchi et al. J. Med. Chem. 1995, 38, 2521) (308 mg, 1.80 mmol) in anhydrous THF (10 mL) was added phosgene (0.89 mL of a 20% solution in toluene, 1.80 mmol), then triethylamine (0.25 mL, 1.80 mmol). The resulting solution was stirred at 0° C. for 1 h, then N-(cyclopropylmethyl)prop-2-en-1-amine from Step A (200 mg, 1.80 mmol) was added, followed by triethylamine (0.75 mL, 5.40 mmol). The reaction mixture was allowed to warm to ambient temperature and stirring was continued for 18 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product, which was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 90:10 to provide the title compound. MS: m/z=309 (M+1).

後処理

  1. temperatureto warm to ambient temperature
  2. stirringstirring
  3. waitwas continued for 18 h
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was partitioned between EtOAc and water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a crude product, which
  10. customwas purified by silica gel chromatography
  11. washeluting with a gradient of hexane

出典と根拠

ORDレコード
ord-4bfd651d5eb8453a818b1240339a761c
出典データセット
uspto-grants-2010_02
特許番号
US07659300B2

反応ノート

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