Hydrochloric Acid → {4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonylamino}-acetic acid

HRID 1685760노트

반응식

HRID 1685760 반응식
C([O:3][C:4](=[O:20])[CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[NH:19])[NH:17][OH:18])=[CH:12][CH:11]=1)(=[O:9])=[O:8])C.[CH2:21]([N:23]([CH2:26][C:27]1[S:31][C:30]([C:32](O)=O)=[CH:29][C:28]=1[CH3:35])[CH2:24][CH3:25])[CH3:22].Cl>[Li+].[OH-].CO>[CH2:21]([N:23]([CH2:26][C:27]1[S:31][C:30]([C:32]2[O:18][N:17]=[C:16]([C:13]3[CH:12]=[CH:11][C:10]([S:7]([NH:6][CH2:5][C:4]([OH:3])=[O:20])(=[O:8])=[O:9])=[CH:15][CH:14]=3)[N:19]=2)=[CH:29][C:28]=1[CH3:35])[CH2:24][CH3:25])[CH3:22]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 672654805-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acidHCID 178472928HCID 178472928, 화합물

생성물 1

HCID 67265676{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonylamino}-acetic acid수율 1.8%

시약·촉매·용매 2

HCID 887Methanol용매HCID 3939Lithium Hydroxide용매

실험 절차

{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonylamino}-acetic acid ethyl ester (98 mg) is obtained starting from [4-(N-hydroxycarbamimidoyl)-benzenesulfonylamino]-acetic acid ethyl ester (233 mg, 0.774 mmol) and 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (160 mg, 0.704 mmol) according to Method A; LC-MS: tR=0.57 min; [M+1]+=493.17. This material (98 mg, 199 μmol) is dissolved in 2 N aq. LiOH (25 mL) and methanol (25 mL). The mixture is stirred at rt for 20 h before it is acidified by adding 1 N aq. HCl and extracted twice with EA. The combined organic extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by prep. HPLC to give the title compound (6 mg) as a white solid; LC-MS: tR=0.50 min; [M+1]+=465.02.

후처리

  1. extractionextracted twice with EA
  2. dry with materialThe combined organic extracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by prep

출처 및 근거

ORD 기록
ord-c0d9b36298bd4f348e8a9beccd73de7c
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148410B2

반응 노트

불러오는 중…