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

HRID 1941549노트

반응식

HRID 1941549 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

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

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-84146c44fa174e97b39eabb7c92e2fea
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05703125

반응 노트

불러오는 중…