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Water → 4-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxylic acid

HRID 2361404
ノート
印刷プレビュー

反応式

HRID 2361404 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:38])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([Br:31])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:32]([O:34]CC)=[O:33])=[N:20][C:19]=2[CH3:37])[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].O>O1CCCC1.CO>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:38])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([Br:31])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:32]([OH:34])=[O:33])=[N:20][C:19]=2[CH3:37])[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67995215ethyl 4-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxylate

生成物 1

HCID 679947674-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxylic acid収率 85%

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of ethyl 4-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxylate (1.36 g, 2.38 mmol) and lithium hydroxide, monohydrate (0.399 g, 9.50 mmol) in tetrahydrofuran (30 mL), methanol (10 mL), and water (12 mL) was stirred at room temperature for 4 h. The solvent was removed under reduced pressure, and the residue was suspended in water (˜20 mL) and 1N aqueous hydrochloric acid (9.5 mL). The pH was adjusted to 5 with 1N aqueous sodium hydroxide, and the suspension was stirred for 60 min. The solid was collected by vacuum filtration, washed with water, and dried overnight to give 4-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxylic acid (1.10 g, 2.02 mmol, 85% yield) as a yellow solid. LC/MS M+1=544.3 and 546.3.

後処理

  1. customThe solvent was removed under reduced pressure
  2. stirringthe suspension was stirred for 60 min
  3. filtrationThe solid was collected by vacuum filtration
  4. washwashed with water
  5. customdried overnight

出典と根拠

ORDレコード
ord-c9e16b4a6b8f462f90b79208ef73cb03
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08685969B2

反応ノート

読み込み中…

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