D-Lysine → 4-[(S)-amino(carboxy)methyl]-3-methylbenzoic acid

HRID 343924

反応式

HRID 343924 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:12]([OH:14])=[O:13])[NH2:11])=[C:6]([CH3:15])[CH:5]=1)([OH:3])=[O:2].N[C@@H](C(O)=O)CCCCN>O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[C:6]([CH3:15])[CH:5]=1)([OH:3])=[O:2]

参加物

4

反応物 2

HCID 57449D-LysineHCID 39317054-[Amino(carboxy)methyl]-3-methylbenzoic acid

生成物 1

HCID 53112614-[(S)-amino(carboxy)methyl]-3-methylbenzoic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Racemic 2-(4-carboxy-2-methylphenyl)glycine (9.2 g, 44 mmol) and D-lysine (6.43 g, 44 mmol) were dissolved in warm water (60 ml). The solution was filtered to remove trace insolubles and then diluted with methanol (200 ml) and diethyl ether (20 ml). An initial precipitate was removed by filtration and the filtrate allowed to stand. After 6 hours the supernatant was decanted from solid and the solid washed with methanol. The solid was then re-crystallised twice from water-methanol and the resulting crystals washed with water-methanol (1:1), methanol and diethyl ether. The white crystals were dried in vacuo, dissolved in water and chromatographed on ion exchange (Dowex 50×8-100 resin). The column was eluted with water, and 10% pyridine in water, fractions collected from the pyridine-water elution were combined and evaporated to dryness. The product was partially dissolved in water and freeze-dried [α]D26 at 147° C. (C=0.26) in aqueous hydrochloric acid (5M).

後処理

  1. filtrationThe solution was filtered
  2. customto remove trace insolubles
  3. additiondiluted with methanol (200 ml) and diethyl ether (20 ml)
  4. customAn initial precipitate was removed by filtration
  5. customAfter 6 hours the supernatant was decanted from solid
  6. washthe solid washed with methanol
  7. customThe solid was then re-crystallised twice from water-methanol
  8. washthe resulting crystals washed with water-methanol (1:1), methanol and diethyl ether
  9. customThe white crystals were dried in vacuo
  10. dissolutiondissolved in water
  11. customchromatographed on ion exchange (Dowex 50×8-100 resin)
  12. washThe column was eluted with water, and 10% pyridine in water, fractions
  13. customcollected from the pyridine-water elution
  14. customevaporated to dryness
  15. dissolutionThe product was partially dissolved in water
  16. dry with materialfreeze-dried [α]D26 at 147° C. (C=0.26) in aqueous hydrochloric acid (5M)

出典と根拠

ORDレコード
ord-1574ac88c5054a00a590985f6b3cfe9d
出典データセット
uspto-grants-1999_01
特許番号
US05863947

関連ノート

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