Triethylamine → N-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(phenylsulfonylmethyl)cyclohexyl)-4-oxo-4-(3-(trifluoromethyl)phenyl)butanamide

HRID 1591737노트

반응식

HRID 1591737 반응식
[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH:33]([N:36]([CH3:54])[C@@H:37]1[CH2:42][CH2:41][C@H:40]([NH2:43])[C@H:39]([CH2:44][S:45]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)(=[O:47])=[O:46])[CH2:38]1)([CH3:35])[CH3:34].[OH-].[Na+]>C1COCC1>[CH:33]([N:36]([CH3:54])[C@@H:37]1[CH2:42][CH2:41][C@H:40]([NH:43][C:5](=[O:7])[CH2:4][CH2:3][C:2](=[O:1])[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C@H:39]([CH2:44][S:45]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)(=[O:46])=[O:47])[CH2:38]1)([CH3:35])[CH3:34]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 62365Isobutyl chloroformateHCID 134088364-Oxo-4-(3-trifluoromethylphenyl)butyric acidHCID 68468828(1R*,3R*,4S*)-N1-isopropyl-N1-methyl-3-(phenylsulfonylmethyl)cyclohexane-1,4-diamine

생성물 1

HCID 11249846N-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(phenylsulfonylmethyl)cyclohexyl)-4-oxo-4-(3-(trifluoromethyl)phenyl)butanamide수율 62.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Commercially available 4-oxo-4-(3-trifluoromethylphenyl)butyric acid (45.5 mg, 0.185 mmol) was dissolved in dry THF (3 mL). To the above solution was added triethyl amine (18.7 mg, 0.185 mmol) and isobutyl chloroformate (25.3 mg, 0.185 mmol) at 0° C. The mixture was stirred at 0° C. for 5 min. before the solution of (1R,3R,4S)—N1-isopropyl-N1-methyl-3-(phenylsulfonylmethyl)cyclohexane-1,4-diamine (see 30b) (50 mg, 0.154 mmol) in dry THF (3 mL) was added. The resulting mixture was warmed up to room temperature. The reaction was completed by 0.5 h. The mixture was treated with 1 N NaOH (5 mL) and extracted with CH2Cl2 (10 mL×2) The organic extracts were washed with water, brine and evaporated. The residue was chromatographed on silica gel (4% NH4OH/MeOH/CH2Cl2) to give the product (53 mg). MS found:(M+1)+: 553.32

후처리

  1. additionwas added
  2. extractionextracted with CH2Cl2 (10 mL×2) The organic extracts
  3. washwere washed with water, brine
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (4% NH4OH/MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-807b265725e84e9ab74f17861c12730f
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291615B2

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