Hydrochloric Acid → 1-Amino-11-azido-3,6,9-trioxaundecane

HRID 882658ノート

反応式

HRID 882658 の反応式
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]=[N+]=[N-])=[N+:2]=[N-:3].Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOCC>[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH2:15])=[N+:2]=[N-:3]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 41574921,11-DIAZIDO-3,6,9-TRIOXAUNDECANE

生成物 1

HCID 27352801-Amino-11-azido-3,6,9-trioxaundecane収率 88%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a mechanically, vigorously stirred suspension of 1,11-diazido-3,6,9-trioxaundecane (20.8 g, 0.085 mol) in 5%/o hydrochloric acid (200 ml) was added a solution of triphenylphosphine (19.9 g, 0.073 mol) in ether (150 ml) over 3 hrs at room temperature. The reaction mixture was stirred for additional 24 hrs. The phases were separated and the aqueous phase was extracted with dichloromethane (3×40 ml). The aqueous phase was cooled in an ice/water bath and pH was adjusted to ca 12 by addition of KOH. The product was extracted into dichloromethane (5×50 ml). Combined organic phases were dried (MgSO4). Filtration and evaporation gave 14.0 g (88%) of yellow oil. Analysis by MALDI-TOF mass spectroscopy (matrix: α-cyano-4-hydroxycinnamic acid) gave a M+H peak at 219 as expected. Further characterisation using 1H (500 MHz) and 13C (125 MHz) NMR spectroscopy verified the structure.

後処理

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane (3×40 ml)
  3. temperatureThe aqueous phase was cooled in an ice/water bath
  4. additionby addition of KOH
  5. extractionThe product was extracted into dichloromethane (5×50 ml)
  6. dry with materialCombined organic phases were dried (MgSO4)
  7. filtrationFiltration and evaporation

出典と根拠

ORDレコード
ord-6991668d37c44692a2ed3ac3f4391cd7
出典データセット
uspto-grants-2012_08
特許番号
US08236283B2

反応ノート

読み込み中…