Acetic Acid → (R)-3-(4-(acetoxymethyl)-7-chloro-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate

HRID 132442노트

반응식

HRID 132442 반응식
[C:1]([O:9][C@H:10]([CH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[C:19]([NH2:23])=[C:18]([CH3:24])[C:17]=1[CH2:25][O:26][C:27](=[O:29])[CH3:28])[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C(O)(=O)C.[N:41](OCCC(C)C)=O.C([O-])(=O)C.[K+]>>[C:1]([O:9][C@H:10]([CH2:15][C:16]1[C:17]([CH2:25][O:26][C:27](=[O:29])[CH3:28])=[C:18]2[C:19](=[C:20]([Cl:22])[CH:21]=1)[NH:23][N:41]=[CH:24]2)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 5

HCID 176Acetic AcidHCID 1140TolueneHCID 8053Isoamyl NitriteHCID 517044Potassium AcetateHCID 59732080(R)-3-(2-(acetoxymethyl)-4-amino-5-chloro-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate

생성물 1

HCID 59732064(R)-3-(4-(acetoxymethyl)-7-chloro-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate수율 88%

실험 절차

(R)-3-(2-(acetoxymethyl)-4-amino-5-chloro-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate (16.33 g, 38.9 mmol) in toluene (100.0 ml, 939 mmol) was added acetic acid (5.0 ml, 87 mmol) followed by isoamyl nitrite (5.76 ml, 42.8 mmol) at 0° C. After 15 min, potassium acetate (7.64 g, 78 mmol) was added and the reaction mixture was stirred for 12 h. The solvent was removed and the crude product was dissolved in dichloromethane (250 mL) and washed with aqueous NaHCO3. The solvent was dried (Na2SO4), evaporated and the crude product was purified by flash chromatography using 40% EtOAc in hexane to give (R)-3-(4-(acetoxymethyl)-7-chloro-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate in 88% yield. MS (ESI) 453 (M+Na); Rf=2.46.

후처리

  1. customThe solvent was removed
  2. dissolutionthe crude product was dissolved in dichloromethane (250 mL)
  3. washwashed with aqueous NaHCO3
  4. dry with materialThe solvent was dried (Na2SO4)
  5. customevaporated
  6. customthe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-03ba4303370a4273a163ff076e35f686
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384931B2

반응 노트

불러오는 중…