Lithium Hydroxide → 3-[[4-[[4-(Aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]hexanedioic acid

HRID 1941549ノート

反応式

HRID 1941549 の反応式
[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:31])[CH2:12][CH2:13][C:14]([NH:16][CH:17]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])[CH2:18][C:19]([O:21]CC)=[O:20])=[O:15])=[CH:6][CH:5]=1.[OH-].[Li+].C(O)(C(F)(F)F)=O>O.C(#N)C>[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:31])[CH2:12][CH2:13][C:14]([NH:16][CH:17]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 70062228Diethyl3-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]hexanedioate

生成物 1

HCID 700611703-[[4-[[4-(Aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]hexanedioic acid収率 57.4%

試薬・触媒・溶媒 1

HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

Diethyl 3-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]hexanedioate (700 mg) prepared in Example 19, Step 2 was added to water/acetonitrile (20 ml) followed by lithium hydroxide (150 mg) at 25° C. The mixture was stirred for 30 min. The course of the reaction was monitored by RPHPLC. After satisfactory product was formed the reaction was neutralized with TFA and purified by reverse phase chromatography (0.05% TFA water/acetonitrile) to result in 350 mg of a white solid: H NMR (d6 -DMSO) δ1.55 (m, 1H), 1.7 (m, 1H), 2.3 (m, 2H), 2.57 (m, 2H), 2.67 (m, 2H), 4.03 (m, 1H), 7.79 (s, 4H), 7.99 (d, 1H, J=8 Hz), 8.86 (bs, 2H), 9.17 (bs, 2H), 10.2 (s, 1H); MS (FAB) m/z 379.2 (MH+).

後処理

  1. customAfter satisfactory product was formed the reaction
  2. custompurified by reverse phase chromatography (0.05% TFA water/acetonitrile)

出典と根拠

ORDレコード
ord-84146c44fa174e97b39eabb7c92e2fea
出典データセット
uspto-grants-1997_12
特許番号
US05703125

反応ノート

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