Hydrochloric Acid → (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-1-[(2-aminothiazol-4-yl)methyl]-5-phenyl-2H-1,4-benzodiazepine-2-one

HRID 1769862노트

반응식

HRID 1769862 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][CH:13]1[N:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]([CH2:30][C:31]2[N:32]=[C:33]([NH:36]C(=O)C)[S:34][CH:35]=2)[C:14]1=[O:40])=[O:11].CO.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O.O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][CH:13]1[N:19]=[C:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]([CH2:30][C:31]2[N:32]=[C:33]([NH2:36])[S:34][CH:35]=2)[C:14]1=[O:40])=[O:11]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 14800361(3RS)-1,3-dihydro-3-(2-indolylcarbonyl-amino)-1-[(2-acetamidothiazol-4-yl)methyl]-5-phenyl-2H-1,4-benzodiazepine-2-one

생성물 1

HCID 14800362(3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-1-[(2-aminothiazol-4-yl)methyl]-5-phenyl-2H-1,4-benzodiazepine-2-one

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

A mixture of (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-1-[(2-acetamidothiazol-4-yl) methyl ] -5-phenyl-2H-1,4-benzodiazepine-2-one, methanol (13 ml), tetrahydrofuran (8 ml ) and conc. hydrochloric acid (0.8 ml ) was stirred for 7.0 hours at 70° C., cooled and adjusted to pH 7.0 with aqueous solution of sodium bicarbonate. To the mixture were added water (100 ml) and ethyl acetate (100 ml) under cooling. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel with an eluent of a mixture of ethyl acetate and chloroform (2:1) to give (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-1-[(2-aminothiazol-4-yl)methyl]-5-phenyl-2H-1,4-benzodiazepine-2-one.

후처리

  1. temperaturecooled
  2. temperatureunder cooling
  3. washThe separated organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel with an eluent of a mixture of ethyl acetate and chloroform (2:1)

출처 및 근거

ORD 기록
ord-aae52c3bbd1940c78bb565b2b417e077
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05382664

반응 노트

불러오는 중…