Hydrochloric Acid → 4-(((1r)-3-Hydroxy-1-((phenylthio)methyl)propyl)amino)-3-nitrobenzenesulfonamide

HRID 1785821노트

반응식

HRID 1785821 반응식
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C@@H:12]([CH2:17][S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][C:14](O)=[O:15])=[C:7]([N+:25]([O-:27])=[O:26])[CH:6]=1)(=[O:4])=[O:3].B.CO.Cl>C1COCC1.C(OCC)(=O)C>[OH:15][CH2:14][CH2:13][C@@H:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([NH2:1])(=[O:4])=[O:3])=[CH:6][C:7]=1[N+:25]([O-:27])=[O:26])[CH2:17][S:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 11683013(r)-3-(2-Nitro-4-sulfamoylphenylamino)-4-(phenylthio)butanoic acid

생성물 1

HCID 684535934-(((1r)-3-Hydroxy-1-((phenylthio)methyl)propyl)amino)-3-nitrobenzenesulfonamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of Example 122E (206 mg, 0.50 mmol) and 1M borane in THF (20 mL) was stirred for 16 hours, treated sequentially with methanol (5.0 mL) and 1N HCl (2.0 mL), diluted with ethyl acetate (50 mL), washed with water (2 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/dichloromethane to provide the desired product. MS (ESI(+)) m/e 398 (M+H)+.

후처리

  1. washwashed with water (2 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/dichloromethane

출처 및 근거

ORD 기록
ord-a67cc521a5ee4cbb948d924c7a59089c
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504512B2

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