Glycine → FG 4592

HRID 523975

反応式

HRID 523975 の反応式
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[C:5]([CH3:19])=[N:4][C:3]=1[C:20](OC)=[O:21].[NH2:24][CH2:25][C:26]([OH:28])=[O:27].C[O-].[Na+].NCC([O-])=O.[Na+]>CO>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[C:5]([CH3:19])=[N:4][C:3]=1[C:20]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:21]

参加物

6

反応物 4

HCID 750GlycineHCID 4684308Sodium GlycinateHCID 10942334Sodium Methoxide2 回HCID 712448953-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl ester

生成物 1

HCID 11256664FG 4592収率 86.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
110 °C

実験手順

A pressure flask was charged with 3e (30.92 g), glycine (22.52 g), methanol (155 mL), sodium methoxide solution (64.81 g) and sealed (as an alternative, sodium glycinate was used in place of glycine and sodium methoxide). The reaction was heated to about 110° C. until reaction was complete. The mixture was cooled, filtered, washed with methanol, dried under vacuum, dissolved in water and washed with ethyl acetate. The ethyl acetate was removed and to the resulting aqueous layer an acetic acid (18.0 g) solution was added. The suspension was stirred at room temperature, filtered, and the solid washed with water (3×30 mL), cold acetone (5-10° C., 2×20 mL), and dried under vacuum to obtain 2-(4-hydroxy-1-methyl-7-phenoxyisoquinoline-3-carboxamido)acetic acid (Yield: 86.1%, HPLC: 99.8%).

後処理

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washwashed with methanol
  4. customdried under vacuum
  5. dissolutiondissolved in water
  6. washwashed with ethyl acetate
  7. customThe ethyl acetate was removed and to the resulting aqueous layer an acetic acid (18.0 g) solution
  8. additionwas added
  9. filtrationfiltered
  10. washthe solid washed with water (3×30 mL), cold acetone (5-10° C., 2×20 mL)
  11. customdried under vacuum

出典と根拠

ORDレコード
ord-07705635484f42dcbae9b04aa3cbbdd9
出典データセット
uspto-grants-2016_05
特許番号
US09340511B2

関連ノート

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