Glycine → FG 4592

HRID 523975

반응식

HRID 523975 반응식
[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]

참가 물질

6

반응물 4

HCID 750GlycineHCID 4684308Sodium GlycinateHCID 10942334Sodium Methoxide2회HCID 712448953-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl ester

생성물 1

HCID 11256664FG 4592수율 86.1%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
110 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-07705635484f42dcbae9b04aa3cbbdd9
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340511B2

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