Propylene Oxide → alpha-Amino-3-(phosphonomethyl)-2-quinoxalinepropanoic Acid

HRID 892411ノート

反応式

HRID 892411 の反応式
BrCC1C(CBr)=NC2C(=CC=CC=2)N=1.C([O:17][C:18](=[O:37])[CH:19]([NH2:36])[CH2:20][C:21]1[C:30]([CH2:31][P:32]([OH:35])([OH:34])=[O:33])=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1)C.[OH-].[K+].C1OC1C>O>[NH2:36][CH:19]([CH2:20][C:21]1[C:30]([CH2:31][P:32]([OH:34])([OH:35])=[O:33])=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1)[C:18]([OH:37])=[O:17]

参加物

6

反応物 4

HCID 6378Propylene OxideHCID 14797Potassium HydroxideHCID 184492,3-Bis(bromomethyl)quinoxalineHCID 10315115alpha-Amino-3-(phosphonomethyl)-2-quinoxalinepropanoic acid ethyl ester

生成物 1

HCID 10470686alpha-Amino-3-(phosphonomethyl)-2-quinoxalinepropanoic Acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

The crude hydrobromide of α-amino-3-(phosphonomethyl)-2-quinoxalinepropanoic acid ethyl ester (1.4 mmole, 600 mg) was added to 1N aqueous potassium hydroxide (5.75 mL). The mixture was stirred overnight at room temperature, and then applied to an ion-exchange column (20 mL volume, Amberlite IRA 400) which had been prewashed with deionized water (40 mL). The column was washed to neutrality with deionized water, and the elution was continued with 0.5N hydrochloric acid. The acidic eluate was evaporated to dryness under reduced pressure, the residue was stripped with water (2×30 mL), benzene (2×30 mL), and dissolved in ethanol (10 mL). This solution was treated with propylene oxide (14.5 mmole, 1 mL), stirred for 30 minutes, the precipitate was collected by filtration, washed successively with cold ethanol and diethyl ether, and dried in vacuo at 85° C. The α-amino-3-(phosphonomethyl)-2-quinoxalinepropanoic acid (300 mg) melted at 176° C. with decomposition; MS (pos. FAB) 312 (MH+ ); 1H NMR (D2O, 400 MHz): δ3.29 (dd, J1 =21 Hz, J2 =6 Hz, 2H, CH2 --P), 3.69 (m, 2H, CH2), 4.41 (m, 1H, CH), 7.56 (m, 2H, ArH), 7.71 and 7.81 (m, 2H, ArH).

後処理

  1. washThe column was washed to neutrality with deionized water
  2. washthe elution
  3. customThe acidic eluate was evaporated to dryness under reduced pressure
  4. dissolutiondissolved in ethanol (10 mL)
  5. stirringstirred for 30 minutes
  6. filtrationthe precipitate was collected by filtration
  7. washwashed successively with cold ethanol and diethyl ether
  8. customdried in vacuo at 85° C

出典と根拠

ORDレコード
ord-d3e5ef38cb3d422abd5acba1c0326f5c
出典データセット
uspto-grants-1992_06
特許番号
US05118675

反応ノート

読み込み中…