Hydrochloric Acid → HCID 89668260, 화합물

HRID 1482207노트

반응식

HRID 1482207 반응식
[C:1](Cl)(=[O:17])[O:2][CH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15].[NH2:19][C@@H:20]([CH2:24][S:25][S:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:21]([OH:23])=[O:22].C(=O)([O-])[O-].[Na+].[Na+].Cl.Br[CH2:39][C:40]#[N:41].C(N(C(C)C)C(C)C)C.[Cl-].[NH4+]>O1CCOCC1.O.CN(C=O)C>[C:27]([S:26][S:25][CH2:24][C@H:20]([NH:19][C:1]([O:2][CH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15])=[O:17])[C:21]([O:23][CH2:39][C:40]#[N:41])=[O:22])([CH3:30])([CH3:29])[CH3:28]

참가 물질

11

반응물 7

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11534BromoacetonitrileHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 3084878((Nitroveratryl)oxy)chlorocarbamateHCID 7006457s-tert-Butylmercapto-L-cysteine2회

생성물 1

HCID 89668260HCID 89668260, 화합물수율 98%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

실험 절차

4,5-Dimethoxy-2-nitrobenzyl carbonochloridate (694 mg, 2.52 mmol) was added to a solution of (R)-2-amino-3-(tert-butyldisulfanyl)propanoic acid (Compound 2f-E, 500 mg, 2.29 mmol) and sodium carbonate (534 mg, 5.04 mmol) in dioxane (5 ml) and water (5 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was then adjusted to pH 2 by adding 1 N hydrochloric acid, and was extracted by adding ethyl acetate. The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. 2-Bromoacetonitrile (0.284 ml, 4.08 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.285 ml, 1.63 mmol) were added to a solution of the resulting residue in DMF (6 ml), and the mixture was stirred at room temperature for 20 minutes. A saturated aqueous ammonium chloride solution (3 ml) was added to the reaction mixture, after which the mixture was extracted with ethyl acetate and the organic layer was washed with water. The organic extract was then dried over magnesium sulfate. Following concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→60/40) to afford (R)-cyanomethyl 3-(tert-butyldisulfanyl)-2-((((4,5-dimethoxy-2-nitro benzyl)oxy)carbonyl)amino)propanoate (Compound 21-E) (653 mg, 98%).

후처리

  1. extractionwas extracted
  2. additionby adding ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. stirringthe mixture was stirred at room temperature for 20 minutes
  7. extractionafter which the mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with water
  9. extractionThe organic extract
  10. dry with materialwas then dried over magnesium sulfate
  11. concentrationconcentration under reduced pressure
  12. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→60/40)

출처 및 근거

ORD 기록
ord-e473ca4f1ca5411a9e1a212f2c1c4027
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409952B2

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