Hydrochloric Acid → N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)-amino)sulfonyl)benzoyl)-L-glutamic acid

HRID 1377069

반응식

HRID 1377069 반응식
[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([NH:17][S:18]([C:21]4[CH:42]=[CH:41][C:24]([C:25]([NH:27][C@H:28]([C:36]([O:38]CC)=[O:37])[CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])=[O:26])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.Cl>[OH-].[Na+]>[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([NH:17][S:18]([C:21]4[CH:22]=[CH:23][C:24]([C:25]([NH:27][C@H:28]([C:36]([OH:38])=[O:37])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:26])=[CH:41][CH:42]=4)(=[O:20])=[O:19])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 136147908diethyl N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)amino)sulfonyl)benzoyl)-L-glutamate

생성물 1

HCID 136076379N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)-amino)sulfonyl)benzoyl)-L-glutamic acid

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
50 °C

실험 절차

A solution of diethyl N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)amino)sulfonyl)benzoyl)-L-glutamate (0.175 g, 0.3 mmoles) in 1N NaOH (12 ml) was stirred and heated to 50° C. under a nitrogen atmosphere for 24 hrs. After cooling, the solution was acidified (pH 3) with concentrated HCl to cause precipitation of the product which was filtered, washed with water and dried to give N-(4-(((3-amino-1,2 -dihydro-1-oxobenzo[f]quinazolin-9-yl)-amino)sulfonyl)benzoyl)-L-glutamic acid as an off-white solid. (0.18 g, 99%) 1HNMR (DMSO-d6, 300 MHz) δ: 1.81-2.13(m, 2H, glu-CH2); 2.32(t, J=7.6 Hz, 2H, glu-CH2); 4.34(m, 1H, glu-CH); 6.58(br s, 2H, NH2); 7.16(d, J =Hz, 1H, Ar); 7.22(dd, J=8.6, 2 Hz, 1H, Ar); 7.74(d, J=8.7 Hz, 1H, Ar); 7.89(d, J=9.0 Hz, 1H, Ar); 7.96(m, 4H, Ar); 8.78(d, J=7.16 Hz, 1H, glu-NH); g.4 g(d, J=2 Hz, 1H, Ar); 10.68(s, 1H, 11.1(br s, 1H, NH); 12.3(br s, 2H, (CO2H)2). Anal. Calculated for C24H21N5O8S.3H2O; C, 48.56; H, 4.58; N, 11.80; S, 5.40. Found: C, 48.38; H, 4.30; N, 11.69; S, 5.34.

후처리

  1. temperatureAfter cooling
  2. customprecipitation of the product which
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

출처 및 근거

ORD 기록
ord-8f5984c834fb4843946d8413793d9efe
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663337

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