Lansoprazole → Dexlansoprazole

HRID 16932

反応式

HRID 16932 の反応式
[CH3:1][C:2]1[C:3]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:4][CH:5]=[N:6][C:7]=1[CH2:8][S+:9]([O-:19])[C:10]1[NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[N:18]=1.CCCCCC.C(N(CC)CC)C.CCCCCC.CC(O)C>CC(O)C>[CH3:1][C:2]1[C:7]([CH2:8][S@:9]([C:10]2[NH:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[N:18]=2)=[O:19])=[N:6][CH:5]=[CH:4][C:3]=1[O:20][CH2:21][C:22]([F:25])([F:23])[F:24]

参加物

6

反応物 4

HCID 3883LansoprazoleHCID 8058HexaneHCID 8471TriethylamineHCID 21585144Isopropanol hexane

生成物 1

HCID 9578005Dexlansoprazole収率 27.2%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

Lansoprazole (racemate) (34.2 g) was dissolved in 2-propanol (1,710 ml) and hexane (1,140 ml) containing triethylamine (0.2%) and fractionated by HPLC (column: CHIRALCEL OD 50 mm dia.×500 mm, temperature: room temperature, mobile phase: hexane/2-propanol=85/15, flow rate: 60 ml/min, detection wavelength: 285 nm, 1 shot: about 300 mg) to isolate the individual optical isomers. Fractions of an optical isomer of shorter retention time were combined and concentrated; the individual lots were combined and dissolved in ethanol (250 ml); after triethylamine (3 ml) was added, the solution was filtered through a 0.45 μm filter. After the filtrate was concentrated, hexane was added, and the filtrate was again evaporated to dryness to yield R(+)-lansoprazole (9.31 g, optical purity 98.3% ee) as an amorphous substance.

後処理

  1. customto isolate the individual optical isomers
  2. concentrationconcentrated
  3. dissolutiondissolved in ethanol (250 ml)
  4. additionafter triethylamine (3 ml) was added
  5. filtrationthe solution was filtered through a 0.45 μm
  6. filtrationfilter
  7. concentrationAfter the filtrate was concentrated
  8. additionhexane was added
  9. customthe filtrate was again evaporated to dryness

出典と根拠

ORDレコード
ord-8a05a436f6a74f90915a0150f499cd3e
出典データセット
uspto-grants-2010_06
特許番号
US07737282B2

関連ノート

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