1,2-Dichloroethane → HCID 22977492, 화합물

HRID 2363376노트

반응식

HRID 2363376 반응식
C([O:5][C:6](=O)[NH:7][CH:8]([C:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[C:20](=[O:36])[NH:21][CH:22]1[CH2:26][C:25](=[O:27])[O:24][CH:23]1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O.CCN(C(C)C)C(C)C.[NH2:54][C:55]1[CH:63]=[CH:62][C:58](C(O)=O)=[CH:57][C:56]=1[Cl:64].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[CH2:29]([O:28][CH:23]1[CH:22]([NH:21][C:20]([CH:16]2[CH2:17][CH2:18][CH2:19][N:15]2[C:13](=[O:14])[CH:8]([NH:7][C:6](=[O:5])[C:58]2[CH:62]=[CH:63][C:55]([NH2:54])=[C:56]([Cl:64])[CH:57]=2)[C:9]([CH3:12])([CH3:10])[CH3:11])=[O:36])[CH2:26][C:25](=[O:27])[O:24]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

참가 물질

8

반응물 6

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 172114-Amino-3-chlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68655183{1-[2-(2-Benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-pyrrolidine-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid tert-butyl ester

생성물 1

HCID 22977492HCID 22977492, 화합물수율 527.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 456 mg (0.088 mmol) of 71 in CH2Cl2 (20 ml) was treated with anhydrous TFA (5 mL) then stirred at room temperature under N2 for 1 hour and evaporated to dryness. The residue was repeatedly concentrated from CH2Cl2 (3×) then dried under vacuum. The resulting residue was dissolved in CH2Cl2 (20 ml), cooled to 0° C., then treated with DIEA (1.3 ml, 8 eq, 2.46 mmol) followed by 4-amino-3-chloro-benzoic acid (202 mg, 1.17 mmol), HOBT (183 mg, 1.35 mmol), and EDC (279 mg, 1.45 mmol). The resulting mixture was allowed to warm to room temperature and stir for 18 hours. The solvent was removed in vacuo and the residue dissolved in EtOAc then washed with distilled water (3×), 0.5N NaHSO4 (2×), saturated NaHCO3 (2×) and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give a residue that was purified by flash chromatography, eluting with CH2Cl2/MeOH (99/1 to 97/3%), affording 265 mg (57% yield) of the title compound (72) as a yellow solid.

후처리

  1. customevaporated to dryness
  2. concentrationThe residue was repeatedly concentrated from CH2Cl2 (3×)
  3. customthen dried under vacuum
  4. dissolutionThe resulting residue was dissolved in CH2Cl2 (20 ml)
  5. temperaturecooled to 0° C.
  6. temperatureto warm to room temperature
  7. stirringstir for 18 hours
  8. customThe solvent was removed in vacuo
  9. dissolutionthe residue dissolved in EtOAc
  10. washthen washed with distilled water (3×), 0.5N NaHSO4 (2×), saturated NaHCO3 (2×) and brine
  11. dry with materialThe organic layer was dried over Na2SO4
  12. filtrationfiltered
  13. customevaporated
  14. customto give a residue that
  15. customwas purified by flash chromatography
  16. washeluting with CH2Cl2/MeOH (99/1 to 97/3%)

출처 및 근거

ORD 기록
ord-fc8d146eb62a40c295b803ed9a1590ef
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691848B2

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