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Dimethylamine → (R)-N,N-Dimethyl-3-[(2-nitro-4-sulfamoylphenyl)amino]-4-phenylsulfanylbutanamide

HRID 1785777
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HRID 1785777 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].[CH3:28][NH:29][CH3:30].CCN=C=NCCCN(C)C>C1COCC1.CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[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]([N:29]([CH3:30])[CH3:28])=[O:15])=[C:7]([N+:25]([O-:27])=[O:26])[CH:6]=1)(=[O:4])=[O:3]
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참가 물질

8

반응물 3

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11683013(r)-3-(2-Nitro-4-sulfamoylphenylamino)-4-(phenylthio)butanoic acid

생성물 1

HCID 11553925(R)-N,N-Dimethyl-3-[(2-nitro-4-sulfamoylphenyl)amino]-4-phenylsulfanylbutanamide

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6228
Dimethylformamide
용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of Example 122E (411 mg, 1 mmol), 2M dimethylamine in THF (1 mL), EDCI (296 mg, 1.5 mmol), and DMAP (10 mg ) in DMF (10 mL) at room temperature was stirred for 16 hours, diluted with ethyl acetate (200 mL), washed sequentially with 1N HCl (50 mL), water (50 mL), and brine (20 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 100% ethyl acetate to provide the desired product. MS (ESI(+)) m/e 439 (M+H)+.

후처리

  1. washwashed sequentially with 1N HCl (50 mL), water (50 mL), and brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 100% ethyl acetate

출처 및 근거

ORD 기록
ord-b1900dfb586a4827895dad053a5a117b
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07504512B2

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